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

HRID 868247ノート

反応式

HRID 868247 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d42b7ef0faf479f9d20f70b6bbe1844
出典データセット
uspto-grants-1988_10
特許番号
US04778790

反応ノート

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