2-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline → (R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(N-(2-bromo-4-methylaminosulfonylmethylphenyl)-N-trifluoroacetylamino)propene

HRID 975015Notes

Reaction equation

HRID 975015 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH:16]=[CH:17][CH2:18]O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:20][C:21]1[CH:33]=[C:32]([CH2:34][S:35]([NH:38][CH3:39])(=[O:37])=[O:36])[CH:31]=[CH:30][C:22]=1[NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH:16]=[CH:17][CH2:18][N:23]([C:22]1[CH:30]=[CH:31][C:32]([CH2:34][S:35]([NH:38][CH3:39])(=[O:37])=[O:36])=[CH:33][C:21]=1[Br:20])[C:24](=[O:29])[C:25]([F:26])([F:28])[F:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 110032962-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylanilineHCID 54485243(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene

Product 1

HCID 54094024(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(N-(2-bromo-4-methylaminosulfonylmethylphenyl)-N-trifluoroacetylamino)propeneYield 44%

Procedure

(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene and 2-bromo-4-methylaminosulfonylmethyl-N-trifluoroacetylaniline were used. Column chromatography using elution with 4% acetone in methylene chloride afforded the title compound as a white foam (44%): FAB LRMS (m/z, relative intensity) 620 ([MH+ with 81Br], 618 ([MH+ with 79Br], 98), 576 (50), 574 (63), 512 (17), 484 (33).

Workup

  1. washelution with 4% acetone in methylene chloride

Sources & evidence

ORD record
ord-3ee5518fdab542939cee1bd8d17902b2
Source dataset
uspto-grants-1997_03
Patent number
US05607951

Reaction notes

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