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

HRID 1260323노트

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HRID 1260323 반응식
[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]

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 232838552-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid

생성물 1

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

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온도
90 °C

실험 절차

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)+

후처리

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

출처 및 근거

ORD 기록
ord-a3480e7278ba46a181edf2a930f81c39
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470820B2

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