Methyl bromoacetate → HCID 59732695, compound

HRID 1983311Notes

Reaction equation

HRID 1983311 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[C:23]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[O:14])[S:10][CH:11]=1)=[O:4].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>C1COCC1>[CH3:35][O:34][C:32](=[O:33])[CH2:31][NH:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[C:23]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[O:14])[S:10][CH:11]=1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 86593069HCID 86593069, compound

Product 1

HCID 59732695HCID 59732695, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{[({2-[3-(2-Cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-carbamoyl)-methyl]-amino}-acetic acid methyl ester (44 mg, 88%) was prepared by treating 2-amino-N-{2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-ylmethyl}-acetamide (104 mg, 0.25 mmol) with methyl bromoacetate (0.023 mL, 0.25 mmol) in THF (5 mL) at 60° C. for 2 h followed by column purification [silica, DCM:ethyl acetate (80:20 to 20:80)].

Workup

  1. customfollowed by column purification [silica, DCM:ethyl acetate (80:20 to 20:80)]

Sources & evidence

ORD record
ord-3a25c5e2ceb443a3a8e08a8a66d5be52
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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