Hydrogen Bromide → (-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

HRID 1668357노트

반응식

HRID 1668357 반응식
Br.[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH:16]C(=O)OC)[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1.[OH-].[Na+]>C(O)(=O)C>[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH2:16])[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 86619614methyl (+/-)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

생성물 1

HCID 67359100(-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine수율 87.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A mixture of acetic acid (80 mL) and hydrogen bromide (48%, 40 mL) was added to methyl (±)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate (38.2 mmol), and the mixture stirred overnight at 100° C. After cooling down the reaction mixture was poured into a cold 1N NaOH solution (pH 9). It was extracted with ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and the solvent was evaporated under reduced pressure to yield the crude title compound (12.7 g, 87%) which was used without further purification. (m/z)=381+383 (M+H)+.

후처리

  1. temperatureAfter cooling down the reaction mixture
  2. extractionIt was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-19cefacc63994b60876e97209bb19297
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989442B2

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