Water → HCID 86699734, 화합물

HRID 515163노트

반응식

HRID 515163 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][C:12]=2[O:24]C)=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][C:12]=2[OH:24])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 72187884HCID 72187884, 화합물

생성물 1

HCID 86699734HCID 86699734, 화합물수율 45%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-[(4-chlorophenyl)-methyl]-2-methoxy-6-methyl-4-morpholin-4-yl-benzamide (synthesized according to the methods described in sections a) to f) of example 10) (0.25 g, 0.67 mmol) in dichloromethane (10 ml) is added neat boron tribromide (0.095 ml, 1.0 mmol) at −78° C. The temperature is slowly raised to RT over a period of 30 min and stirred for 1 h at RT. The reaction mixture is poured onto cold water and extracted with dichloromethane (3×30 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude material is purified by column chromatography (silica gel, 40% ethyl acetate/hexane) affording N-[(4-chlorophenyl)-methyl]-2-hydroxy-6-methyl-4-morpholin-4-yl-benzamide (0.11 g, 0.30 mmol, 45%).

후처리

  1. extractionextracted with dichloromethane (3×30 ml)
  2. washThe combined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude material is purified by column chromatography (silica gel, 40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-615ce37c531c4385a1ecab63029ae617
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108936B2

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