(S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester → (S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid

HRID 660677Notes

Reaction equation

HRID 660677 reaction equation
C([O:5][C:6](=[O:47])[C@@H:7]([NH:37][S:38]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=[O:40])=[O:39])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:16]2(=[O:28])=[O:27])=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:41]1([S:38]([NH:37][C@@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:25])([CH3:26])[CH3:24])[S:16]3(=[O:28])=[O:27])=[C:11]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:10]=2)[C:6]([OH:47])=[O:5])(=[O:40])=[O:39])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 1

HCID 68842899(S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

Product 1

HCID 68838051(S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of (S)-2-benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid tert-butyl ester (80 mg, 0.114 mmol) in 12 mL of TFA/CH2Cl2 (5:1) is stirred at RT for 1 h. The solution is concentrated, then four times redissolved in CH2Cl2 and reconcentrated to give the title compound: (M−1)−=644.

Workup

  1. concentrationThe solution is concentrated
  2. dissolutionfour times redissolved in CH2Cl2

Sources & evidence

ORD record
ord-cc0e21d06e834e55846ba6b36bcac439
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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