HCID 86584060, compound → HCID 86584059, compound

HRID 843724Notes

Reaction equation

HRID 843724 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][C@@H:8]([CH2:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[NH:9]C(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:30])[CH2:7][C@@H:8]([CH2:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[NH2:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86584060HCID 86584060, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86584059HCID 86584059, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-(benzyloxycarbonyl)-3(S)-phenylsulfonylmethy-β-alanine tert-butyl ester (0.44 g) and 10% Pd—C (0.1 g, 50% wet) in acetic acid (5 ml) was hydrogenated at 1 atmospheric pressure of hydrogen for 1 hour. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous NaHCO3 solution. The organic layer was dried over MgSO4 and evaporated in vacuo to give 3(S)-phenylsulfonylmethy-βalanine tert-butyl ester (0.3 g) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaHCO3 solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c7dd75df140f4dd49d921ef9a454e644
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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