Acryloyl chloride → HCID 86674086, 화합물

HRID 337214노트

반응식

HRID 337214 반응식
C(N(C(C)C)CC)(C)C.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:35])[C:27]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1.[C:36](Cl)(=[O:39])[CH:37]=[CH2:38]>C(Cl)Cl>[C:36]([NH:10][CH:11]1[CH2:12][CH2:13][N:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([N:26]([CH3:35])[C:27]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])=[CH:24][CH:25]=2)(=[O:18])=[O:19])[CH2:15][CH2:16]1)(=[O:39])[CH:37]=[CH2:38]

참가 물질

5

반응물 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 71079543HCID 71079543, 화합물

생성물 1

HCID 86674086HCID 86674086, 화합물수율 18.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Diisopropylethylamine (0.34 ml, 2.1 mmol) was added in one portion to a stirred solution of tetrahydro-pyran-4-carboxylic acid [4-(4-amino-piperidine-1-sulfonyl)-phenyl]-methyl-amide (0.17 g, 0.4 mmol) in DCM (10 ml), followed by the drop wise addition of acryloyl chloride (0.04 ml, 0.42 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (20 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered, concentrated and the resulting residue was purified by flash column chromatography (elution: 97% EtOAc, 3% Methanol) to give the title compound (0.032 g, 18% yield) as a white solid.

후처리

  1. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe resulting residue was purified by flash column chromatography (elution: 97% EtOAc, 3% Methanol)

출처 및 근거

ORD 기록
ord-1b7547f75133406b8930af660babf263
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

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