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

HRID 1260323Notes

Reaction equation

HRID 1260323 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
90 °C

Procedure

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)+

Workup

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

Sources & evidence

ORD record
ord-a3480e7278ba46a181edf2a930f81c39
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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