Ethanol → HCID 67138779, compound

HRID 1592058Notes

Reaction equation

HRID 1592058 reaction equation
C([O:8][C:9](=[O:43])[C@@H:10]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([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:13]=1)C1C=CC=CC=1.CCO.[H][H]>CCOC(C)=O.[Pd]>[C:39]([O:38][C:36]([NH:35][C@@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([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:33])=[O:34])[CH:13]=1)[C:9]([OH:43])=[O:8])=[O:37])([CH3:40])([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 702EthanolHCID 67139722(S)-2-t-butoxycarbonylamino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67138779HCID 67138779, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The title D compound, (S)-2-t-butoxycarbonylamino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid benzyl ester (187 mg, 0.307 mmol) is dissolved in a 1:1 mixture of EtOAc:EtOH (50 mL) in a 200 mL Parr bottle. 10% Palladium on carbon (52 mg) is added as a solid and the reaction mixture is hydrogenated on a Parr Shaker Apparatus at 47 psi of hydrogen for 1.33 h. The reaction mixture is filtered through celite and concentrated in vacuo to give (S)-2-t-butoxycarbonylamino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid as a white foam: [M−1]−=518.1.

Workup

  1. filtrationThe reaction mixture is filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e35f9384108a4fbbb941fc561b47f039
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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