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

HRID 868247Notes

Reaction equation

HRID 868247 reaction equation
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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1d42b7ef0faf479f9d20f70b6bbe1844
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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