Bis(2-((tert-butyldiphenylsilyl)oxy)ethyl)amine → (R)-N,N-Bis(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanamide

HRID 1476276Notes

Reaction equation

HRID 1476276 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](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:32]([O:49][CH2:50][CH2:51][NH:52][CH2:53][CH2:54][O:55][Si:56]([C:69]([CH3:72])([CH3:71])[CH3:70])([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([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]([CH2:53][CH2:54][O:55][Si:56]([C:69]([CH3:72])([CH3:71])[CH3:70])([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[C:11](=[O:12])[CH2:10][C@@H:9]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](=[O:23])(=[O:24])[NH2:22])=[CH:17][C:16]=1[S:25]([C:28]([F:29])([F:31])[F:30])(=[O:27])=[O:26])[CH2:8][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:45]([CH3:46])([CH3:47])[CH3:48])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 11146292Bis(2-((tert-butyldiphenylsilyl)oxy)ethyl)amine2×HCID 66723519(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid2×

Product 1

HCID 86661867(R)-N,N-Bis(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanamideYield 83.1%

Procedure

The title product (1.06 g, yield: 83%) 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, 600 mg, 1.2 mmol) and bis(2-(tert-butyldiphenylsilyloxy)ethyl)amine (INTERMEDIATE 29, 0.700 g, 1.20 mmol) as starting materials. The title product was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes).

Workup

  1. customThe title product was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5afb47cfdbd64f84936c0994d3019213
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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