Acetone → HCID 57445189、化合物

HRID 2405838ノート

反応式

HRID 2405838 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 57445189HCID 57445189、化合物収率 64%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-6b9fbe0ca1074947b5285c1d1229b909
出典データセット
uspto-grants-2014_08
特許番号
US08809267B2

反応ノート

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