1,2-Dibromoethane → t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

HRID 1668573노트

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HRID 1668573 반응식
[OH:1][C:2]1[C:19]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Br[CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH3:24][S:21]([N:20]1[C:19]2=[CH:18][C:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=3[CH:3]=[C:2]2[O:1][CH2:27][CH2:26]1)(=[O:23])=[O:22]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 591504841,1-dimethylethyl 7-hydroxy-8-[(methylsulfonyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

생성물 1

HCID 58494859t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

1,1-dimethylethyl 7-hydroxy-8-[(methylsulfonyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (0.55 g) and 1,2-dibromoethane (0.23 ml) in the presence of potassium carbonate (0.4 g) were heated in acetone/water (1/1, 8 ml) for 6 h at reflux. Volatiles were evaporated under reduced pressure, the residue was partitioned between aqueous NaHCO3 and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined organic layers were concentrated and submitted to column chromatography to provide the title compound (0.75 mmol) as a white slightly hygroscopic solid. MS (m/z): 383 [MH]+.

후처리

  1. temperatureat reflux
  2. customVolatiles were evaporated under reduced pressure
  3. customthe residue was partitioned between aqueous NaHCO3 and DCM
  4. customThe organic layer was collected
  5. extractionthe aqueous phase extracted twice with DCM
  6. concentrationThe combined organic layers were concentrated

출처 및 근거

ORD 기록
ord-4eae36581c734448984006f544313666
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989444B2

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