tert-Butanol → (2-Pyridin-2-yl-thiazol-5-yl)-carbamic acid tert-butyl ester

反応式

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:8][C:9](C(O)=O)=[CH:10][N:11]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:34]([CH2:37]C)CC)C.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:37](=[O:22])[NH:34][C:9]1[S:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:11][CH:10]=1)([CH3:42])([CH3:41])[CH3:40]

参加物

反応物 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 232838552-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid

生成物 1

HCID 67299899(2-Pyridin-2-yl-thiazol-5-yl)-carbamic acid tert-butyl ester

反応条件

温度: 90 °C

実験手順

A solution of 2-pyridin-2-yl-thiazol-5-carboxylic acid (250 mg, 1.2 mmol) in tert-butanol (4.5 ml) was treated with diphenylphosphoryl azide (0.4 ml, 1.85 mmol) and triethylamine (0.34 ml, 2.4 mmol) and stirred at 90° C. for 5 h. The reaction mixture was extracted with ethyl acetate and the combined organic phases were washed with saturated ammonium acetate solution, water and brine. The final product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as yellow oil (180 mg, 54%). MS: M=278.2 (M+H)+

後処理

extractionThe reaction mixture was extracted with ethyl acetate
washthe combined organic phases were washed with saturated ammonium acetate solution, water and brine

出典と根拠

ORDレコード: ord-a3480e7278ba46a181edf2a930f81c39
出典データセット: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08470820B2

反応ノート

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