2768-53-8 → L-alanyl-L-phenylalanine

HRID 1086313Notes

Reaction equation

HRID 1086313 reaction equation
C(OC([NH:11][C@H:12]([C:14]([NH:16][C@H:17]([C:25]([OH:27])=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH3:13])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][C@H:17]([C:25]([OH:27])=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 69991262768-53-8

Product 1

HCID 96814L-alanyl-L-phenylalanineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine (0.208 g, 0.562 mmol) and 10% Pd on carbon (0.1 g) in 95% ethyl alcohol (50 mL) was shaken on a Parr hydrogenation apparatus for 16 h at 20° C. The reaction mixture was filtered and the filtrate rinsed with water (100 mL). The combined solutions were concentrated to give 0.122 g (92%) of L-alanyl-L-phenylalanine as a white solid. HPLC analysis showed >99.5% purity and no evidence of racemization.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate rinsed with water (100 mL)
  3. concentrationThe combined solutions were concentrated

Sources & evidence

ORD record
ord-a0cbb5bec2204442acbc1a870c2570db
Source dataset
uspto-grants-1991_07
Patent number
US05028693

Reaction notes

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