1-[2-(Acetylthio)-1-oxoethyl]-4-[(2-furyl)methyl]-4-hydroxy-L-proline → 4-[(2-furyl)methyl]-4-hydroxy-L-proline

HRID 223735Notes

Reaction equation

HRID 223735 reaction equation
C([N:11]1[CH2:18][C:17]([CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.C(SCC(N1CC(CC2OC=CC=2)(O)C[C@H]1C(O)=O)=O)(=O)C>>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[CH2:20][C:17]1([OH:19])[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Participants

3

Reactant 2

HCID 541477931-[2-(Acetylthio)-1-oxoethyl]-4-[(2-furyl)methyl]-4-hydroxy-L-prolineHCID 54161613N-carbobenzyloxy-4-[(2-furyl)methyl]-4-hydroxy-L-proline2×

Product 1

HCID 541343924-[(2-furyl)methyl]-4-hydroxy-L-proline

Procedure

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

Sources & evidence

ORD record
ord-6f3d0f8ebbf640878818e697dc27e1b2
Source dataset
uspto-grants-1982_10
Patent number
US04356182

Reaction notes

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