1-(L-alanyl)-4-(S)-(phenylthio)-L-proline, phenylmethyl ester → 1-(L-alanyl)-4-(S)-(phenylthio)-L-proline

HRID 1463022Notes

Reaction equation

HRID 1463022 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][C@@H:19]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][C@H:7]1[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:3].[H][H]>[Pd].C(O)C>[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][C@@H:19]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Participants

5

Reactant 2

HCID 1317135931-(L-alanyl)-4-(S)-(phenylthio)-L-proline, phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 228271961-(L-alanyl)-4-(S)-(phenylthio)-L-proline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5.0 grams of 1-(L-alanyl)-4-(S)-(phenylthio)-L-proline, phenylmethyl ester in 200 ml. of aqueous ethanol there is added 1 gram of freshly prepared palladium black and the mixture is hydrogenated at 50 psi of hydrogen. The reaction mixture is filtered and concentrated under reduced pressure to yield the desired (S)-1-(L-alanyl)-4-(phenylthio)-L-proline.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7315f6cee2224c87ae076bcdf66b5c50
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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