(S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-(4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl)-propionic acid benzyl ester → (S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid

HRID 1592052Notes

Reaction equation

HRID 1592052 reaction equation
C([O:8][C:9](=[O:50])[C@@H:10]([NH:35][C:36](=[O:49])[C@@H:37]([NH:45][C:46](=[O:48])[CH3:47])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][C:21](=[O:23])[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:19]2(=[O:34])=[O:33])=[CH:14][CH:13]=1)C1C=CC=CC=1>CCOC(C)=O.CCO.[Pd]>[C:46]([NH:45][C@@H:37]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:36]([NH:35][C@@H:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:22][C:21](=[O:23])[N:20]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[S:19]2(=[O:34])=[O:33])=[CH:16][CH:17]=1)[C:9]([OH:50])=[O:8])=[O:49])(=[O:48])[CH3:47]

Participants

4

Reactant 1

HCID 67138247(S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-(4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl)-propionic acid benzyl ester

Product 1

HCID 67139907(S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

The title B compound, (S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid benzyl ester (104.3 mg, 0.149 mmol) is dissolved in EtOAc:EtOH (50:50; 250 mL) and put in a Parr Shaker bottle along with 10% Palladium on carbon (30 mg). This gas in the bottle is evacuated and replaced with hydrogen at 45 psi and shaken for 1.5 h. The reaction mixture is filtered through celite and concentrated to yield (S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid as a light yellow foam.

Workup

  1. customThis gas in the bottle is evacuated
  2. filtrationThe reaction mixture is filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-da2d8ac9a40f4f7e90e8a13d638f23e6
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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