N-Carbobenzyloxy-4-hydroxy-4-[(4-pyridyl)methyl]-L-prolin → 4-hydroxy-4-[(4-pyridyl)methyl]-L-proline

HRID 223738Notes

Reaction equation

HRID 223738 reaction equation
C([N:11]1[CH2:18][C:17]([OH:26])([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.C(SCC(N1CC=C[C@@]1(CC1OC=CC=1)C(O)=O)=O)(=O)C>>[OH:26][C:17]1([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Participants

3

Reactant 2

HCID 53928413N-Carbobenzyloxy-4-hydroxy-4-[(4-pyridyl)methyl]-L-prolin2×HCID 57067544(2S)-1-[2-(Acetylthio)-1-oxoethyl]-[(2-furyl)methyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid

Product 1

HCID 539451174-hydroxy-4-[(4-pyridyl)methyl]-L-proline

Procedure

The N-carbobenzyloxy-4-hydroxy-4-[(4-pyridyl)-methyl]-L -proline from part (a) is hydrogenated according to the procedure of Example 1 (b) to yield 4-hydroxy-4-[(4-pyridyl)methyl]-L-proline. This amino acid is reacted with D-3-acetylthio-2-methylpropionyl chloride according to the procedure of Example 1 (c) to yield [1(S)]-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-4-hydroxy-4-[(4-pyridyl)methyl]-L-proline.

Sources & evidence

ORD record
ord-f85f6d68ac7f4590b5f0d2befba3a907
Source dataset
uspto-grants-1982_10
Patent number
US04356182

Reaction notes

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