Water → HCID 20244757, compound

HRID 482760Notes

Reaction equation

HRID 482760 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]([CH:17]([NH:26][CH:27]1[CH2:33][CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[NH:29][C:28]1=[O:38])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].O>O1CCCC1>[CH2:7]([O:14][C:15]([CH:17]([NH:26][CH:27]1[CH2:33][CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[N:29]([CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:28]1=[O:38])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79177tert-Butyl bromoacetateHCID 13243514HCID 13243514, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20244757HCID 20244757, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (1.2 g) was added to a solution of 3-(1-benzyloxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (3.0 g) and t-butyl bromoacetate (2.2 g) in tetrahydrofuran (100 ml) stirring at room temperature under an atmosphere of dry nitrogen. The reaction mixture was stirred for 20 hours at room temperature, then poured into water (250 ml) and extracted with dichloromethane (2×150 ml). The combined dichloromethane solutions were washed with water (100 ml) and dried over magnesium sulfate. Evaporation of the solvent gave 3-(1-benzyloxycarbonyl-3-phenylpropylamino)-1-t-butyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one.

Workup

  1. stirringThe reaction mixture was stirred for 20 hours at room temperature
  2. extractionextracted with dichloromethane (2×150 ml)
  3. washThe combined dichloromethane solutions were washed with water (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e8f0f6c88e8849278877d1833332d5e2
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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