Benzenesulfonyl chloride → (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

HRID 660676Notes

Reaction equation

HRID 660676 reaction equation
[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH2:37])[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)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:46]1([S:52](Cl)(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CC#N>[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH:37][S:52]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(=[O:54])=[O:53])[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:27])=[O:28])=[C:11]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 68839983(S)-2-Amino-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 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (S)-2-amino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid tert-butyl ester (Example 132, step C) (10 mg, 0.249 mmol) and triethylamine (51 mg, 0.5 mmol) in MeCN (5 mL) is added benzenesulfonyl chloride (44 mg, 0.249 mmol) and the mixture is stirred at RT for 2 h. The solvent is removed under reduced pressure and the residue partitioned between methylene chloride and 1N HCl. The organic phase dried over sodium sulfate and the solvent removed under reduced pressure. The residue is purified by flash chromatography using a gradient of 0-40% EtOAc/hexane as eluent to give the title compound: (M−1)−=700.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue partitioned between methylene chloride and 1N HCl
  3. dry with materialThe organic phase dried over sodium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4ac5342c3ab742e7a2f7d650461ab03b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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