Triethylamine → tert-butyl 9-hydroxy-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

HRID 1514224노트

반응식

HRID 1514224 반응식
Br.[O:2]1[C:8]2[C:9]([OH:13])=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[O:21](C(OC(C)(C)C)=O)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=O>ClCCl>[OH:13][C:9]1[C:8]2[O:2][CH2:3][CH2:4][N:5]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[CH2:6][C:7]=2[CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 684690182,3,4,5-Tetrahydro-1,4-benzoxazepin-9-ol hydrobromide

생성물 1

HCID 59403444tert-butyl 9-hydroxy-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate수율 100.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A suspension of 2,3,4,5-tetrahydro-1,4-benzoxazepin-9-ol. hydrobromide (Preparation 85) (55.7 g, 226 mmol) in dichloromethane (DCM) (550 ml) was treated with triethylamine (47.3 ml, 339 mmol) and stirred for 20 minutes. This mixture was cooled in ice/water to ca 5° C. and treated slowly with a solution of BOC2O (59.6 ml, 249 mmol) in dichloromethane (DCM) (200 ml) at such a rate as to keep the internal temperature below 10° C. When the addition was complete, the mixture was allowed to warm to room temperature, stirred for 2 hours and allowed to stand at room temperature overnight. The mixture was washed with 0.5M hydrochloric acid (2×250 ml) and water (250 ml), dried (sodium sulphate) and evaporated to give the title compound as a pale brown solid (60.5 g)

후처리

  1. customthe internal temperature below 10° C
  2. additionWhen the addition
  3. stirringstirred for 2 hours
  4. waitto stand at room temperature overnight
  5. washThe mixture was washed with 0.5M hydrochloric acid (2×250 ml) and water (250 ml)
  6. dry with materialdried (sodium sulphate)
  7. customevaporated

출처 및 근거

ORD 기록
ord-6c418fbcc1284fcc895539f4f246bd2f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222245B2

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