2,4-Dichlorothiazole → (S)-methyl 2-(tert-butoxycarbonyl)-3-(4-chlorothiazol-2-yl)propanoate

HRID 1009129

Reaction equation

HRID 1009129 reaction equation
[C:1]([O:5][C:6]([C@H:8]([CH2:13]I)[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[S:17][CH:18]=[C:19]([Cl:21])[N:20]=1>>[C:1]([O:5][C:6]([C@@H:8]([CH2:13][C:16]1[S:17][CH:18]=[C:19]([Cl:21])[N:20]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 123331552,4-DichlorothiazoleHCID 86614124(R)-methyl2-(tert-butoxycarbonyl)-3-iodopropanoate

Product 1

HCID 67305732(S)-methyl 2-(tert-butoxycarbonyl)-3-(4-chlorothiazol-2-yl)propanoate

Procedure

The title compound was synthesized in a manner analogous to that described Example 475, using (R)-methyl 2-(tert-butoxycarbonyl)-3-iodopropanoate and 2,4-dichlorothiazole (prepared according to Reynaud, Pierre; Robba, Max; Moreau, Robert C; New synthesis of the thiazole ring; Bulletin de la Societe Chimique de France (1962), 1735-8). MS m/z: 321 (23%, M+1), 265.0 (100%, M−55.1).

Workup

  1. customprepared
  2. customNew synthesis of the thiazole ring

Sources & evidence

ORD record
ord-d618dc6f90b7403f807a6bbdd51653c7
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Linked notes

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