Acetone → HCID 57445189, 화합물

HRID 1893688노트

반응식

HRID 1893688 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[O:9][CH:10]=1)=[O:5])[CH3:2].[CH3:12][C:13]([CH3:15])=O.S(C)C.B>C1COCC1.CC(O)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][CH:13]([CH3:15])[CH3:12])[O:9][CH:10]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 180AcetoneHCID 1068Dimethyl SulfideHCID 6331BoraneHCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylate

생성물 1

HCID 57445189HCID 57445189, 화합물수율 64%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-aminooxazole-4-carboxylic acid ethyl ester (500 mg, 3.2 mmol) and acetone (2.4 mL, 32 mmol) in THF (6 mL) was stirred at rt. BH3.SMe2 (10M in THF, 0.64 mL, 6.4 mmol) was added slowly via syringe (exotherm and gas evolution were observed). AcOH (0.36 mL, 6.4 mmol) was subsequently added in the same manner. Two additional equivalents of borane and AcOH were added 18 h later. After 3 days at rt, the reaction mixture was concentrated in vacuo. The resulting residue was dissolved in EtOAc (100 mL), washed with saturated NH4Cl solution, 0.1 M NH4OH and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with EtOAc/hexane to give 2-isopropylamino-oxazole-4-carboxylic acid ethyl ester (0.40 g, 64% yield). LCMS found 199 [M+H]+.

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc (100 mL)
  3. washwashed with saturated NH4Cl solution, 0.1 M NH4OH and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluting with EtOAc/hexane

출처 및 근거

ORD 기록
ord-c7a25a13dc90412692768a9deae19ca3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513186B2

반응 노트

불러오는 중…