Dimethyl Disulfide → 4-(5-Methylsulfanyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1352302Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16](Br)=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21]SC>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]([S:21][CH3:20])=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 12232Dimethyl Disulfide

HCID 34180719Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperazine-1-carboxylate

Product 1

HCID 684067784-(5-Methylsulfanyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 78%

Procedure

Prepared in analogy to example 4 (b) from 4-(5-bromo-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (Example 4(a)) and dimethyl disulphide. The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a yellow crystalline solid (yield 78%). MS (m/e): 316.3 (M+H+, 100%).

Workup

customThe crude material was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-026f3f60fbe4417ca396988e36afa285
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220744B2

Reaction notes

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