HCID 67138423, compound → HCID 67139048, compound

HRID 1591987Notes

Reaction equation

HRID 1591987 reaction equation
C([O:8][C:9](=[O:44])[C@@H:10]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]2[CH2:23][C:22](=[O:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[S:20]2(=[O:35])=[O:34])[CH:13]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.CCO.[Pd]>[C:40]([O:39][C:37]([NH:36][C@@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]2[CH2:23][C:22](=[O:24])[N:21]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[S:20]2(=[O:34])=[O:35])[CH:13]=1)[C:9]([OH:44])=[O:8])=[O:38])([CH3:41])([CH3:43])[CH3:42]

Participants

5

Reactant 2

HCID 67138423HCID 67138423, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67139048HCID 67139048, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

The title D compound, (S)-2-t-butoxycarbonylamino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-propionic acid benzyl ester (127 mg, 0.20 mmol) is dissolved in EtOAc/EtOH (50:50) (56 mL) and 10% palladium on carbon (35 mg) is added and the mixture is treated with 45 psi of hydrogen on a Parr shaker apparatus. After two 90 min runs, starting material is not completely consumed, so another aliquot of 10% palladium on carbon (35 mg) is added and after shaking at 45 psi hydrogen for 30 min, the reaction is complete. The mixture is filtered through celite, the filtrate is concentrated and dried to give (S)-2-t-butoxycarbonylamino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-propionic acid as a white foam: [M+1]+=534.

Workup

  1. customAfter two 90 min
  2. customis not completely consumed
  3. additionso another aliquot of 10% palladium on carbon (35 mg) is added
  4. filtrationThe mixture is filtered through celite
  5. concentrationthe filtrate is concentrated
  6. customdried

Sources & evidence

ORD record
ord-0ec1947bdcbb4ba0b783b06ed2e6bf3d
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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