Sodium Iodide → t-Butyl rel-alpha-{3(S)-[5-(1-t-butoxycarbonyl-4piperidyl)-1-ethoxycarbonylpentylamino]-2-oxo-6(R)phenylperhydroazepin-1-yl}acetate

HRID 868247노트

반응식

HRID 868247 반응식
Br[CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:25][C@H:26]1[CH2:32][CH2:31][C@H:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][N:28]([CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:27]1=[O:47].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C.CN(C)C=O>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH:2]([NH:25][C@H:26]2[CH2:32][CH2:31][C@H:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:29][N:28]([CH2:39][C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[C:27]2=[O:47])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 14003452t-butyl rel-alpha-[3(S)-amino-2-oxo-6(R)-phenylperhydroazepin-1-yl]acetateHCID 21287852Ethyl 2-bromo-6-(1-t-butoxycarbonyl4-piperidyl)hexanoate

생성물 1

HCID 22840208t-Butyl rel-alpha-{3(S)-[5-(1-t-butoxycarbonyl-4piperidyl)-1-ethoxycarbonylpentylamino]-2-oxo-6(R)phenylperhydroazepin-1-yl}acetate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1.08 g of ethyl 2-bromo-6-(1-t-butoxycarbonyl4-piperidyl)hexanoate, 0.85 g of t-butyl rel-α-[3(S)amino-2-oxo-6(R)-phenylperhydroazepin-1-yl]acetate, 0.4 g of sodium iodide and 1.4 g of sodium carbonate were added to 15 ml of dimethylformamide, and the mixture was stirred at room temperature for 3 days. Ethyl acetate and water were then added to the reaction mixture, and, after stirring, the ethyl acetate layer was separated, washed with an aquous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography using a 2:1 by volume mixture of cyclohexane and ethyl acetate as the eluent.

후처리

  1. stirringafter stirring
  2. customthe ethyl acetate layer was separated
  3. washwashed with an aquous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by evaporation under reduced pressure
  6. additionby volume mixture of cyclohexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-1d42b7ef0faf479f9d20f70b6bbe1844
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778790

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