Glutaric anhydride → (glutarimidomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester

HRID 476717Notes

Reaction equation

[C:1]1(=[O:8])[O:7][C:5](=O)[CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH2:13]([O:15][P:16]([CH2:36][NH2:37])([CH2:18][CH:19]([C:24](=[O:35])[NH:25][C@H:26]([C:31](=[O:34])[NH:32][CH3:33])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[CH3:14]>>[CH2:13]([O:15][P:16]([CH2:36][N:37]1[C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]1=[O:7])([CH2:18][CH:19]([C:24](=[O:35])[NH:25][C@H:26]([C:31](=[O:34])[NH:32][CH3:33])[CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[CH3:14]

Participants

Reactant 2

HCID 7940Glutaric anhydride

HCID 86743561(aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester acetate

Product 1

HCID 53732201(glutarimidomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl esterYield 27.9%

Procedure

In a manner analogous to that described in Example 24(A), from 0.161 g (1.41 mmol) of glutaric anhydride and 0.41 g (0.94 mmol) of (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester acetate, there was obtained 0.124 g of (glutarimidomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester.

Sources & evidence

ORD record: ord-e2adfacbdf2a4e7ab89c0c99b478f8a5
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885283

Reaction notes

Loading…