Carbon dioxide methanol → HCID 71468692, compound

HRID 240879Notes

Reaction equation

HRID 240879 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:32]([F:35])([F:34])[F:33])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([C:19]([NH:21][C@@H:22]4[CH2:26][CH2:25][NH:24][C:23]4=[O:27])=[O:20])=[C:16]4[CH2:28][CH2:29][CH2:30][CH2:31][C:15]=34)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)=O.CO>>[Cl:8][C:6]1[CH:5]=[C:4]([C@@:9]2([C:32]([F:34])([F:33])[F:35])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([C:19]([NH:21][C@@H:22]4[CH2:26][CH2:25][NH:24][C:23]4=[O:27])=[O:20])=[C:16]4[CH2:28][CH2:29][CH2:30][CH2:31][C:15]=34)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 21973728Carbon dioxide methanolHCID 71467508HCID 71467508, compound

Product 1

HCID 71468692HCID 71468692, compound

Procedure

Separate 3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N—((R)-2-oxopyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamide (6.2 g 11.29 mmol) by SFC (Column: Chiralcel OD 250×30 mm I.D., 5 um. Mobile phase: Supercritical CO2/MeOH=60/40, Flow rate: 200 ml/min) to afford two diastereoisomers 3-((R)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N—((R)-2-ox pyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamide (2.7 g, 4.92 mmol) and 3-((S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N—((R)-2-oxopyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxamide (2.6 g, 4.74 mmol) as a white solid.

Sources & evidence

ORD record
ord-d605415b749546e3ad5bebe3a2b32212
Source dataset
uspto-grants-2014_02
Patent number
US08648081B2

Reaction notes

Loading…