L-Proline → 1-L-Alanyl-D-proline

Reaction equation

N1CCC[C@H]1C(O)=O.[NH2:9][C@@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH3:11]>>[NH2:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH3:11]

Participants

Reactant 2

HCID 145742L-Proline

HCID 6993389(R)-1-((R)-2-Aminopropanoyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 1089851-L-Alanyl-D-proline

Procedure

By substituting D-proline for L-proline in the above example, a 70% diastereomeric excess mixture of D-alanyl-D-proline and L-alanyl-D-proline was obtained.

Sources & evidence

ORD record: ord-7c5c474dbd28494d887887522b80854c
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424454

Reaction notes

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