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

HRID 1771176Notes

Reaction equation

HRID 1771176 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][N:21]([CH2:52]C)[C:22](=[O:51])[CH2:23][C@@H:24]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](=[O:43])(=[O:42])[NH2:41])=[CH:36][C:35]=1[S:44]([C:47]([F:50])([F:49])[F:48])(=[O:46])=[O:45])[CH2:25][S:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(SC[C@H](NC2C=CC(S(=O)(=O)N)=CC=2S(C(F)(F)F)(=O)=O)CC(O)=O)C=CC=CC=1.[Si](OCCNC)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[Si:1]([O:18][CH2:19][CH2:20][N:21]([CH3:52])[C:22](=[O:51])[CH2:23][C@@H:24]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](=[O:42])(=[O:43])[NH2:41])=[CH:36][C:35]=1[S:44]([C:47]([F:50])([F:48])[F:49])(=[O:46])=[O:45])[CH2:25][S:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamine2×HCID 66723519(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid2×HCID 66723918(R)-N-(2-(tert-Butyldiphenylsilyloxy)ethyl)-N-ethyl-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluorom ethylsulfonyl)phenylamino)butanamide

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-55969b53cf26457d856974f075b7df12
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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