Dicyclohexylcarbodiimide → Imidapril tert-Butyl Ester

HRID 1980278Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]([CH3:20])[C:17]([OH:19])=O)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].C1C(=O)N(O)C(=O)C1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:44][N:45]1[CH2:49][C@@H:48]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[NH:47][C:46]1=[O:57]>>[CH3:44][N:45]1[CH2:49][C@@H:48]([C:50]([O:52][C:53]([CH3:55])([CH3:54])[CH3:56])=[O:51])[N:47]([C:17](=[O:19])[C@@H:16]([NH:15][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:20])[C:46]1=[O:57]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 80170N-Hydroxysuccinimide

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

HCID 13053976tert-Butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate

Product 1

HCID 14801864Imidapril tert-Butyl EsterYield 70.5%

Procedure

560 mg of (2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionic acid, 230 mg of 1-hydroxysuccinimide, 413 mg of dicyclohexylcarbodiimide and 400 mg of tert.-butyl (4S)-1-methyl-2-oxo-imidazolidine-4-carboxylate are treated in the same manner as described in Example 1-(1), whereby 650 mg of tert.-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate are obtained as colorless viscous oil. Yield: 70.4%

Sources & evidence

ORD record: ord-600f4108d3644d898409dfe98c164bc6
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04508727

Reaction notes

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