1-[4-(Acetylthio)-1-oxobutyl]-4-hydroxy-4-[(4-methyl)phenyl]-L-proline → 4-hydroxy-4-[(4-methyl)phenyl]-L-proline

HRID 223725Notes

Reaction equation

HRID 223725 reaction equation
C([N:11]1[CH2:18][C:17]([OH:26])([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.C(SCCCC(N1CC(O)(C2C=CC(C)=CC=2)C[C@H]1C(O)=O)=O)(=O)C>>[OH:26][C:17]1([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Participants

3

Reactant 2

HCID 228174921-[4-(Acetylthio)-1-oxobutyl]-4-hydroxy-4-[(4-methyl)phenyl]-L-prolineHCID 22817588N-carbobenzyloxy-4-hydroxy-4-[(4-methyl)phenyl]-L-proline2×

Product 1

HCID 228175804-hydroxy-4-[(4-methyl)phenyl]-L-proline

Procedure

The N-carbobenzyloxy-4-hydroxy-4-[(4-methyl)phenyl]-L-proline form part (a) is hydrogenated according to the procedure of Example 1 (b) to yield 4-hydroxy-4-[(4-methyl)phenyl]-L-proline. This amino acid is then reacted with 4-acetylthiobutyroyl chloride according to the procedure of Example 1 (c) to yield 1-[4-(acetylthio)-1-oxobutyl]-4-hydroxy-4-[(4-methyl)phenyl]-L-proline.

Sources & evidence

ORD record
ord-f1cfc039a278482eb943a0cc329052a7
Source dataset
uspto-grants-1982_10
Patent number
US04356182

Reaction notes

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