2-Chloro-6-methylbenzoyl chloride → N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester

HRID 844892Notes

Reaction equation

HRID 844892 reaction equation
[C:1]([O:4][CH:5]([O:7][C:8](=[O:29])[C@H:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19](=[O:28])[N:20]([CH3:27])[C:21](=[O:26])[N:22]([CH3:25])[C:23]=2[CH3:24])=[CH:14][CH:13]=1)[NH2:10])[CH3:6])(=[O:3])[CH3:2].[Cl:30][C:31]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:32]=1[C:33](Cl)=[O:34]>>[C:1]([O:4][CH:5]([O:7][C:8](=[O:29])[C@H:9]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:19](=[O:28])[N:20]([CH3:27])[C:21](=[O:26])[N:22]([CH3:25])[C:23]=2[CH3:24])=[CH:16][CH:17]=1)[NH:10][C:33]([C:32]1[C:36]([CH3:40])=[CH:37][CH:38]=[CH:39][C:31]=1[Cl:30])=[O:34])[CH3:6])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 223820402-Chloro-6-methylbenzoyl chlorideHCID 693358374-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester

Product 1

HCID 10120246N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester

Procedure

N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester was prepared from 4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 1-(acetoxy)ethyl ester and 2-chloro-6-methylbenzoyl chloride using the general procedures described in example 33 and was obtained as a white solid: mp 84-88° C. ES-HRMS m/e calcd for C28H30ClN3O7 (M+Na) 578.1664, found 578.1665.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-faf6df88ab6144eabea896afb84e172a
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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