1,2-Dichloroethane → Methyl (2S)-2-{5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrate

HRID 1251906Notes

Reaction equation

HRID 1251906 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[C:14]([CH:18]=2)[C:15](O)=[O:16])[CH:6]=1.Cl.[CH3:34][O:35][C:36](=[O:43])[C@H:37]([CH2:39][CH2:40][S:41][CH3:42])[NH2:38].C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[C:14]([CH:18]=2)[C:15]([NH:38][C@@H:37]([CH2:39][CH2:40][S:41][CH3:42])[C:36]([O:35][CH3:34])=[O:43])=[O:16])[CH:6]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 183244045-[2-(4-Methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acid

Product 1

HCID 57103056Methyl (2S)-2-{5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfanylbutyrateYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoic acid (0.4 g; 0.89 mM), L-methionine methyl ester hydrochloride (0.27 g, 1.35 mM) and DMAP (0.54 g, 4.43 mM) was stirred until solution and EDC (0.026 g, 1.35 mM) in dichloromethane was added and the mixture stirred for 18 hours. It was purified on silica using dichloromethane then methanol/dichloromethane (5:95) as eluant to give the title product (0.47 g, 89%) as a foam.

Workup

  1. additionwas added
  2. customIt was purified on silica

Sources & evidence

ORD record
ord-f05c14b1537548a2812f9550e8bcb5f6
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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