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

HRID 476719Notes

Reaction equation

[CH2:1]([C@H:5]1[CH2:10][C:9](=[O:11])[O:8][C:6]1=O)[CH:2]([CH3:4])[CH3:3].C(O)(=O)C.[CH2:16]([O:18][P:19]([CH2:39][NH2:40])([CH2:21][CH:22]([C:27](=[O:38])[NH:28][C@H:29]([C:34](=[O:37])[NH:35][CH3:36])[CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH3:17]>>[CH2:16]([O:18][P:19]([CH2:39][N:40]1[C:9](=[O:11])[CH2:10][C@H:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[C:6]1=[O:8])([CH2:21][CH:22]([C:27](=[O:38])[NH:28][C@H:29]([C:34](=[O:37])[NH:35][CH3:36])[CH2:30][CH:31]([CH3:32])[CH3:33])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH3:17]

Participants

Reactant 2

HCID 542752432(S)-isobutylsuccinic anhydride

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

Product 1

HCID 67864058[[(S)-2-isobutylsuccinimido]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl esterYield 42.5%

Procedure

In a manner analogous to that described in Example 24(A), from 0.17 g (1.09 mmol) of 2(S)-isobutylsuccinic anhydride and 0.32 g (0.73 mmol) of (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester acetate, there was obtained 0.16 g of [[(S)-2-isobutylsuccinimido]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester.

Sources & evidence

ORD record: ord-af85b11f1df34d8c86d9d29556da4fda
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885283

Reaction notes

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