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The present invention relates to, inter ...
The present invention relates to process...
L-arginine
![(R/S)-ethyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate](/upload/2026/5/16902f36-b7f0-47e6-8ce6-bc12847f4f4e.png)
(R/S)-ethyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate
![(R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid, L-arginine salt](/upload/2026/5/eb781a8a-b06d-425a-811f-3c0f118d54d1.png)
(R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid, L-arginine salt
| Conditions | Yield |
|---|---|
|
(R/S)-ethyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate;
With
lipase B, Candida antarctica;
In
aq. phosphate buffer; acetonitrile;
at 45 ℃;
pH=7 - 8;
Inert atmosphere;
Enzymatic reaction;
L-arginine;
In
water; isopropyl alcohol;
at 81 ℃;
for 1.25h;
Reagent/catalyst;
Solvent;
Temperature;
|
46.45% |
o-trifluoromethylphenyl bromide
(R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid, L-arginine salt
| Conditions | Yield |
|---|---|
|
Multi-step reaction with 5 steps
1.1: N,N,N,N,-tetramethylethylenediamine; magnesium / iron(III) chloride / tetrahydrofuran / 20 - 30 °C / Inert atmosphere
2.1: thionyl chloride; sulfuric acid / -5 - 20 °C / Inert atmosphere
3.1: caesium carbonate / acetonitrile / 40 - 65 °C / Inert atmosphere
4.1: water / recombinant yeast Lipase B Candida antarctica immobilized on Immobead 150 / acetonitrile / 16 h / 40 °C / pH 7.8 / Inert atmosphere; Enzymatic reaction; Aqueous phosphate buffer
4.2: pH 3.96
5.1: isopropyl alcohol; water / 1 h / 60 °C / Inert atmosphere
With
thionyl chloride; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; water; caesium carbonate; magnesium;
iron(III) chloride;
In
tetrahydrofuran; water; isopropyl alcohol; acetonitrile;
|
|
|
Multi-step reaction with 6 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / -78 °C / Cooling with IPA-dry ice; Inert atmosphere
1.2: 1.5 h / -78 - 20 °C / Cooling with IPA-dry ice; Inert atmosphere
1.3: pH 4 - 5 / Cooling with ice
2.1: hydrogen / palladium 10% on activated carbon / ethanol
3.1: thionyl chloride; sulfuric acid / -5 - 20 °C / Inert atmosphere
4.1: caesium carbonate / acetonitrile / 40 - 65 °C / Inert atmosphere
5.1: water / recombinant yeast Lipase B Candida antarctica immobilized on Immobead 150 / acetonitrile / 16 h / 40 °C / pH 7.8 / Inert atmosphere; Enzymatic reaction; Aqueous phosphate buffer
5.2: pH 3.96
6.1: isopropyl alcohol; water / 1 h / 60 °C / Inert atmosphere
With
n-butyllithium; thionyl chloride; sulfuric acid; water; hydrogen; caesium carbonate;
palladium 10% on activated carbon;
In
tetrahydrofuran; hexanes; ethanol; water; isopropyl alcohol; acetonitrile;
|
|
|
Multi-step reaction with 8 steps
1.1: N,N,N,N,-tetramethylethylenediamine; magnesium / iron(III) chloride / tetrahydrofuran / 20 - 30 °C / Inert atmosphere
2.1: bromine; sulfuric acid; acetic acid / 1.5 h / 40 °C
3.1: n-butyllithium / tetrahydrofuran; hexanes / 0.42 h / -78 °C / Cooling with IPA-dry ice; Inert atmosphere
3.2: 0.83 h / -78 - 20 °C / Cooling with IPA-dry ice; Inert atmosphere
4.1: ethanol; sodium tetrahydroborate / 2 h / 20 °C
5.1: thionyl chloride / 9.5 h / 10 - 50 °C
6.1: caesium carbonate / acetonitrile / 40 - 65 °C / Inert atmosphere
7.1: water / recombinant yeast Lipase B Candida antarctica immobilized on Immobead 150 / acetonitrile / 16 h / 40 °C / pH 7.8 / Inert atmosphere; Enzymatic reaction; Aqueous phosphate buffer
7.2: pH 3.96
8.1: isopropyl alcohol; water / 1 h / 60 °C / Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; thionyl chloride; ethanol; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; water; bromine; caesium carbonate; magnesium; acetic acid;
iron(III) chloride;
In
tetrahydrofuran; hexanes; water; isopropyl alcohol; acetonitrile;
|
|
|
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / -78 °C / Cooling with IPA-dry ice; Inert atmosphere
1.2: 1.5 h / -78 - 20 °C / Cooling with IPA-dry ice; Inert atmosphere
1.3: pH 4 - 5 / Cooling with ice
2.1: hydrogen / palladium 10% on activated carbon / ethanol
3.1: bromine; sulfuric acid; acetic acid / 1.5 h / 40 °C
4.1: n-butyllithium / tetrahydrofuran; hexanes / 0.42 h / -78 °C / Cooling with IPA-dry ice; Inert atmosphere
4.2: 0.83 h / -78 - 20 °C / Cooling with IPA-dry ice; Inert atmosphere
5.1: ethanol; sodium tetrahydroborate / 2 h / 20 °C
6.1: thionyl chloride / 9.5 h / 10 - 50 °C
7.1: caesium carbonate / acetonitrile / 40 - 65 °C / Inert atmosphere
8.1: water / recombinant yeast Lipase B Candida antarctica immobilized on Immobead 150 / acetonitrile / 16 h / 40 °C / pH 7.8 / Inert atmosphere; Enzymatic reaction; Aqueous phosphate buffer
8.2: pH 3.96
9.1: isopropyl alcohol; water / 1 h / 60 °C / Inert atmosphere
With
sodium tetrahydroborate; n-butyllithium; thionyl chloride; ethanol; sulfuric acid; water; hydrogen; bromine; caesium carbonate; acetic acid;
palladium 10% on activated carbon;
In
tetrahydrofuran; hexanes; ethanol; water; isopropyl alcohol; acetonitrile;
|
cyclopentanone
4-chloro-3-trifluoromethylbenzoic acid methyl ester
2-ethoxycarbonyl-1-cyclopentanone
o-trifluoromethylphenyl bromide
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