(1S,2S,4S)-4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide → (1R,2R,4R)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

HRID 1367533Notes

Reaction equation

HRID 1367533 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@H:9]2[CH2:13][C@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:11][C@@H:10]2[O:28][CH3:29])=[O:8])[CH2:5][CH2:4]1)#[N:2]>CCCCCCC.C(O)(C)C>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=3[C:24]([F:27])([F:25])[F:26])(=[O:16])=[O:15])[CH2:11][C@H:10]2[O:28][CH3:29])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 1

HCID 59619475(1S,2S,4S)-4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Product 1

HCID 59619295(1R,2R,4R)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Reagents, catalysts & solvents 1

HCID 21225753Isopropanol heptaneSolvent

Procedure

Racemic (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 58) was subjected to chiral preparative HPLC on Chiralpak AD using heptane/isopropanol 75:25 as eluant. The title compound was eluated as the second peak. MS (EI): 495.1 (M+H)+.

Sources & evidence

ORD record
ord-a0f7f2966e5048659e1d6d138a19bd56
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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