tert-Butanol → tert-Butyl 1,3-thiazol-5-ylcarbamate

HRID 1051415Notes

Reaction equation

HRID 1051415 reaction equation
C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])=CC=1.CC[N:20]([CH2:23][CH3:24])[CH2:21]C.[S:25]1C(C(O)=O)=C[N:27]=[CH:26]1.[C:33]([OH:37])([CH3:36])([CH3:35])[CH3:34]>>[S:25]1[C:23]([NH:20][C:21](=[O:8])[O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:24][N:27]=[CH:26]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 84494Thiazole-5-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 53432624tert-Butyl 1,3-thiazol-5-ylcarbamateYield 40.3%

Conditions

Temperature
90 °C

Procedure

A mixture of DPPA (31.1 g, 113 mmol), Et3N (23.70 mL, 170 mmol) and thiazole-5-carboxylic acid (8.0 g, 61.9 mmol) in tert-BuOH (190 mL) was heated to 90° C. for 12 h in a 500 mL round-bottomed flask. After cooling, the solvent was evaporated in vacuo. The residue was diluted with water. The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic phase was washed with brine, dried, concentrated under reduced pressure to give crude product. The crude product was purified by column chromatography on silica gel (EA/heptane=1/10) to give the title compound (5.0 g, 24.97 mmol, 40.3%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo
  3. additionThe residue was diluted with water
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  5. washThe combined organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give crude product
  9. customThe crude product was purified by column chromatography on silica gel (EA/heptane=1/10)

Sources & evidence

ORD record
ord-61c28727893143bf8ebee5b2c37ff8d8
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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