Methyl chloroformate → HCID 86759540, 화합물

HRID 392638노트

반응식

HRID 392638 반응식
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

참가 물질

5

반응물 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 86586603HCID 86586603, 화합물

생성물 1

HCID 86759540HCID 86759540, 화합물수율 70%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75ae0ff2f0ba498388a32515213829a3
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800648B2

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