2-(tert-butyldiphenylsilyloxy)-N-methylethanamine → (R)-N-(2-(tert-butyldiphenylsilyloxy)ethyl)-N-methyl-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanamide

HRID 1476275Notes

Reaction equation

HRID 1476275 reaction equation
[C:1]1([S:7][CH2:8][C@H:9]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:17][C:16]=2[S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:32]([O:49][CH2:50][CH2:51][NH:52][CH3:53])([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[Si:32]([O:49][CH2:50][CH2:51][N:52]([CH3:53])[C:11](=[O:13])[CH2:10][C@@H:9]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:17][C:16]=1[S:25]([C:28]([F:29])([F:30])[F:31])(=[O:26])=[O:27])[CH2:8][S:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:45]([CH3:47])([CH3:48])[CH3:46])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamine2×HCID 66723519(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid2×

Product 1

HCID 66723792(R)-N-(2-(tert-butyldiphenylsilyloxy)ethyl)-N-methyl-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanamideYield 93%

Procedure

The title product (590 mg, yield: 93%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 24 utilizing (R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid (INTERMEDIATE 8, 400 mg, 0.8 mmol) and 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine (INTERMEDIATE 26, 251 mg, 0.8 mmol) as starting materials. The title product was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→100% EtOAc/hexanes).

Workup

  1. customThe title product was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ce0e22cd4ece44e49f0481d942a52bc9
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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