Methyl chloroformate → HCID 86759540、化合物

HRID 392638ノート

反応式

HRID 392638 の反応式
Cl[C:2]([O:4][CH3:5])=[O:3].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][CH2:17][C@@H:18]2[O:23][C:22]3[C:24]([CH:29]=[CH:30][CH3:31])=[C:25]([NH2:28])[CH:26]=[CH:27][C:21]=3[O:20][CH2:19]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][CH2:17][CH:18]2[O:23][C:22]3[C:24]([CH:29]=[CH:30][CH3:31])=[C:25]([NH:28][C:2]([O:4][CH3:5])=[O:3])[CH:26]=[CH:27][C:21]=3[O:20][CH2:19]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 86586603HCID 86586603、化合物

生成物 1

HCID 86759540HCID 86759540、化合物収率 70%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Methyl chloroformate (2.93 mL, 37.9 mmole) was added to a solution of {(2R)-7-amino-8-[1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methyl-benzenesulfonate (2.35 g, 6.30 mmole) in ethyl acetate (125 mL), followed by the addition of N,N-diisopropylethylamine (5.50 mL, 31.6 mmole) dropwise over a period of 20 minutes. The solution was stirred under nitrogen at room temperature over a period of 10 hours. This solution was then washed with 2N aqueous HCl, saturated aqueous sodium bicarbonate and brine and dried over magnesium sulfate. Filtration, evaporation in vacuum and column chromatography on silica gel with 0.2% methanol/methylene chloride gave the (R)-enantiomer of the title compound as a white foam (1.90 g, 70%). 1H (CDCl3) doublet, 7.8 δ (2 H); doublet, 7.3 δ (3 H); doublet, 6.7 δ (1 H); broad singlet, 6.6 δ (1 H); multiplet, 6.1 δ (2 H); multiplet, 4.4 δ (1 H); multiplet 4.2 δ (3 H); multiplet, 4.0 δ (1 H); singlet, 3.7 δ (3 H); singlet, 2.4 δ (3 H); doublet, 1.9 δ (3 H).

後処理

  1. washThis solution was then washed with 2N aqueous HCl, saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration, evaporation in vacuum and column chromatography on silica gel with 0.2% methanol/methylene chloride

出典と根拠

ORDレコード
ord-75ae0ff2f0ba498388a32515213829a3
出典データセット
uspto-grants-2004_10
特許番号
US06800648B2

反応ノート

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