Acetic Acid → HCID 64268641, compound

HRID 2244361Notes

Reaction equation

HRID 2244361 reaction equation
CC([O-])(C)C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[C-:8].[CH:15]1([N:18]=[C:19]=[S:20])[CH2:17][CH2:16]1.C(O)(=O)C>C1COCC1>[CH2:13]([O:12][C:10]([C:9]1[N:7]=[CH:8][S:20][C:19]=1[NH:18][CH:15]1[CH2:17][CH2:16]1)=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 92463Cyclopropyl isothiocyanateHCID 533707Ethyl isocyanoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 64268641HCID 64268641, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a vigorously stirred solution of 311 mg of potassium tert-butylate (2.77 mmol) in THF (5 ml) were slowly added 5 ml of a THF-solution of 300 mg of ethyl isocyanoacetate (2.52 mmol) and 250 mg of cyclopropyl isothiocyanate (2.52 mmol) at −20° C. The mixture was stirred for 15 min at −20° C. and was then allowed to warm to 0° C. in 1.5 h before 0.3 ml of acetic acid were added. The reaction mixture was concentrated in vacuo to give a residue which was purified by flash column chromatography (heptane/ethyl acetate 95:5 to 75:25) to give 5-cyclopropylamino-thiazole-4-carboxylic acid ethyl ester (198 mg, 37%) as a yellow oil. MS (ISP) 213.1 (M+H)+.

Workup

  1. customat −20° C
  2. additionwere added
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a residue which
  5. customwas purified by flash column chromatography (heptane/ethyl acetate 95:5 to 75:25)

Sources & evidence

ORD record
ord-86200dcb01734306a1f4cbc6a817c78f
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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