Iodobenzene diacetate → 10-Bromo-2-carbamoyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-6-carboxylic acid

HRID 575283노트

반응식

HRID 575283 반응식
CC1(C)N([O])C(C)(C)CCC1.C(OI(C1C=CC=CC=1)OC(=O)C)(=[O:14])C.[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[O:37][CH:36]([CH2:38][OH:39])[CH2:35][N:34]3[CH:40]=[C:41]([C:43]([NH2:45])=[O:44])[N:42]=[C:33]3[C:32]=2[CH:46]=1>ClCCl.O>[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[O:37][CH:36]([C:38]([OH:14])=[O:39])[CH2:35][N:34]3[CH:40]=[C:41]([C:43](=[O:44])[NH2:45])[N:42]=[C:33]3[C:32]=2[CH:46]=1

참가 물질

6

반응물 3

HCID 76724Iodobenzene diacetateHCID 2724126TempoHCID 8669331210-Bromo-6-(hydroxymethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

생성물 1

HCID 8669331110-Bromo-2-carbamoyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-6-carboxylic acid수율 73.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

TEMPO (17 mg, 0.11 mmol, 0.33 equiv) and PhI(OAc)2 (255 mg, 0.79 mmol, 2.37 equiv) were added to a stirred suspension of 10-bromo-6-(hydroxymethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (113 mg, 0.33 mmol, 1.00 equiv) in dichloromethane (4 mL) and water (0.8 mL) at 0° C. After 30 min the resulting mixture was warmed to room temperature and stirred overnight. The reaction was then quenched by the addition sodium bicarbonate and washed with dichloromethane. The pH value of the aqueous solution was adjusted to 2 by 2N hydrogen chloride. The aqueous layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in to 85 mg (crude) of 10-bromo-2-carbamoyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-6-carboxylic acid as a white solid.

후처리

  1. customThe reaction was then quenched by the addition sodium bicarbonate
  2. washwashed with dichloromethane
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-6f0846b897a44948b3136671d9a08c40
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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