Ethyl Acetate → Enalapril Maleate

HRID 481758Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[NH:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=[O:24].CC[O:31][C:32]([CH3:34])=[O:33]>>[CH3:2][CH2:1][O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:21]1[C@H:22]([C:23]([OH:25])=[O:24])[CH2:26][CH2:27][CH2:28]1)=[O:20])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5].[CH:34](/[C:32]([OH:31])=[O:33])=[CH:6]/[C:4]([OH:5])=[O:3]

Participants

Reactant 3

HCID 8857Ethyl Acetate

HCID 145742L-Proline

HCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

Product 1

HCID 5388961Enalapril MaleateYield 77%

Procedure

In ES patent 2,004,804 the preparation of carboxyalkyldipeptides useful as ACE inhibitors is disclosed. N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine is treated with 1,1-carbonyldiimidazole in EtOAc and subsequently with L-proline and enalapril maleate is obtained with a 77% yield.

Workup

customIn ES patent 2,004,804 the preparation of carboxyalkyldipeptides useful as ACE inhibitors

Sources & evidence

ORD record: ord-144515cf7c904447a446d2e6c12d553b
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789597

Reaction notes

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