Potassium Carbonate → (2S,5S)-2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylate

HRID 590676노트

반응식

HRID 590676 반응식
[Br:1][CH:2]1[CH2:23][CH2:22][C:5]2=[CH:6][C:7]3[C:8]4[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][C:9]=4[CH2:10][O:11][C:12]=3[CH:13]=[C:4]2[C:3]1=[O:24].[CH3:25][O:26][C:27]([NH:29][C@@H:30]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:31]([N:33]1[C@@H:37]([CH3:38])[CH2:36][CH2:35][C@H:34]1[C:39]([OH:41])=[O:40])=[O:32])=[O:28].C([O-])([O-])=O.[K+].[K+]>ClCCl>[CH3:25][O:26][C:27]([NH:29][C@@H:30]([C@@H:42]([CH3:45])[CH2:43][CH3:44])[C:31]([N:33]1[C@@H:37]([CH3:38])[CH2:36][CH2:35][C@H:34]1[C:39]([O:41][CH2:19][C:18]([C:15]1[CH:16]=[CH:17][C:8]2[C:7]3[CH:6]=[C:5]4[CH2:22][CH2:23][CH:2]([Br:1])[C:3](=[O:24])[C:4]4=[CH:13][C:12]=3[O:11][CH2:10][C:9]=2[CH:14]=1)=[O:21])=[O:40])=[O:32])=[O:28]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 866883729-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-oneHCID 86723610(2S,5S)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylic acid

생성물 1

HCID 86723609(2S,5S)-2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl 1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a slurry of 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (4.00 g, 8.88 mmol) in dichloromethane (50 mL) was added (2S,5S)-1-((2S,3S)-2-(methoxycarbonylamino)-3-methylpentanoyl)-5-methylpyrrolidine-2-carboxylic acid (2.80 g, 9.32 mmol) and K2CO3 (1.84 g, 13.31 mmol). The resulting slurry was stirred at room temperature for 18 h. The reaction was diluted with dichloromethane and washed with aqueous HCl (0.5 M) and Brine. The aqueous layers were back extracted with dichloromethane (2×), and the combined organic layers were dried over Na2SO4 and concentrated. The crude product was taken directly into the next reaction.

후처리

  1. washwashed with aqueous HCl (0.5 M) and Brine
  2. extractionThe aqueous layers were back extracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was taken directly into the next reaction

출처 및 근거

ORD 기록
ord-e20f73d7ea044d97840e7a0c327a4533
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233974B2

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