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

HRID 575283ノート

反応式

HRID 575283 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f0846b897a44948b3136671d9a08c40
出典データセット
uspto-grants-2015_05
特許番号
US09034866B2

反応ノート

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