HCID 15385777, compound → HCID 15385778, compound

HRID 1862018Notes

Reaction equation

HRID 1862018 reaction equation
[CH2:1]([S:3]([NH:6][C@@H:7]([C:15]([N:17]1[CH2:31][CH2:30][CH2:29][C@H:18]1[C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:5])=[O:4])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([S:3]([NH:6][C@@H:7]([C:15]([N:17]1[CH2:31][CH2:30][CH2:29][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 15385777HCID 15385777, compound

Product 1

HCID 15385778HCID 15385778, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EtSO2-D-Phe-Pro-OBn (28.5 g, 64 mmol) in ethyl acetate (500 mL) was added 10% Pd/C (5 g). The vessel was evacuated and placed under an atmosphere of hydrogen. After stirring for 16 h, the solution was filtered over diatomaceous earth, and the filter pad was then washed twice with methanol and filtered. The combined filtrates were concentrated in vacuo to give 22 g (97%) of off-white solid.

Workup

  1. customThe vessel was evacuated
  2. filtrationthe solution was filtered over diatomaceous earth
  3. washthe filter pad was then washed twice with methanol
  4. filtrationfiltered
  5. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-e16b7a39289d4cd7a6520c952e9d4a1f
Source dataset
uspto-grants-2003_03
Patent number
US06534650B2

Reaction notes

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