L-Proline → HCID 53775406, compound

HRID 903452Notes

Reaction equation

HRID 903452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([CH2:7][CH2:8][C:9]([OH:11])=O)=[O:6].[NH:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([CH2:7][CH2:8][C:9]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18])=[O:11])=[O:6]

Participants

3

Reactant 2

HCID 145742L-ProlineHCID 27578284-(3-Chlorophenyl)-4-oxobutanoic acid

Product 1

HCID 53775406HCID 53775406, compound

Procedure

The preceding compound is converted to 3-[3-chlorobenzoyl]propionic acid, hydroxysuccinimide ester as described in Example 15 and coupled with L-proline as described in Example 16 to give 1-[3-(3-chlorobenzoyl)propionyl]-L-proline. The preceding compound is reacted with bromine in acetic acid as described in Example 20 to give 1-[3-bromo-3-(3-chlorobenzoyl)propionyl]-L-proline. The preceding compound in a mixture of ethanol-water (1:1) is reacted with potassium thioacetate as in Example 21 to give the product of the Example as a glass.

Sources & evidence

ORD record
ord-273aa457a1ae428c9627ad85186c1f99
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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