2,5-Bis(2,2,2-trifluoroethoxy)benzene-1-sulfonyl chloride → (4R)-1-[1-{[2,5-bis (2,2,2-trifluoroethoxy)phenyl]sulfonyl}-5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-in dol-3-yl]-4-hydroxy-N,N-dimethyl-L-prolinamide

HRID 1662591Notes

Reaction equation

HRID 1662591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([N:20]1[CH2:29][C@H:28]([OH:30])[CH2:27][C@H:21]1[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[F:31][C:32]([F:52])([F:51])[CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])=[CH:37][C:36]=1[S:47](Cl)(=[O:49])=[O:48]>>[F:52][C:32]([F:31])([F:51])[CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]([F:44])([F:45])[F:46])=[CH:37][C:36]=1[S:47]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([N:20]2[CH2:29][C@H:28]([OH:30])[CH2:27][C@H:21]2[C:22]([N:24]([CH3:25])[CH3:26])=[O:23])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[C:6]1=[O:11])(=[O:49])=[O:48]

Participants

3

Reactant 2

HCID 27360772,5-Bis(2,2,2-trifluoroethoxy)benzene-1-sulfonyl chlorideHCID 67044068(2S,4R)-1-(5-Chloro-3-(2-methoxyphenyl)-2-oxoindolin-3-YL)-4-hydroxy-N,N-dimethylpyrrolidine-2-carboxamide

Product 1

HCID 59867949(4R)-1-[1-{[2,5-bis (2,2,2-trifluoroethoxy)phenyl]sulfonyl}-5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-in dol-3-yl]-4-hydroxy-N,N-dimethyl-L-prolinamideYield 66.8%

Procedure

With 100 mg of (4R)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxy-N,N-dimethyl-L-prolinamide (levorotatory isomer), which is the compound described in Preparation 3.2 (Isomer B) of the brochure Publication No. WO01/55130, and 89 mg of 2,5-bis (2,2,2-trifluoroethoxy)benzene sulfonyl chloride as starting materials, 119 mg of the title compound (colorless amorphous) was obtained by a similar method to Example 2.

Workup

  1. customdescribed in Preparation 3.2 (Isomer B) of the brochure Publication No

Sources & evidence

ORD record
ord-8348b5f92fa34fa1a6279c94037de063
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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