Water → 4-(2-Benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694904Notes

Reaction equation

HRID 1694904 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:11][C:12](=[O:37])[NH:13][C:14]([CH3:36])([CH3:35])[CH2:15][N:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17](=[O:20])[CH2:18]Br)([CH3:10])([CH3:9])[CH3:8].[Cl-].[NH4+].O>O1CCCC1>[C:7]([O:11][C:12]([N:13]1[CH2:18][C:17](=[O:20])[N:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:15][C:14]1([CH3:36])[CH3:35])=[O:37])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 66645394{2-[(2-Benzyloxyphenyl)-(2-bromoacetyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

Product 1

HCID 666453984-(2-Benzyloxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.59 g of potassium t-butoxide (14.2 mmol) in tetrahydrofuran (100 ml) was added to a solution of 4.64 g of {2-[(2-benzyloxyphenyl)-(2-bromoacetyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester obtained in Example (10b) (9.64 mmol) in tetrahydrofuran (100 ml) under a nitrogen atmosphere and under cooling in a dry ice-acetone bath over 30 minutes, and the mixture was stirred at the same temperature for 10 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture. The mixture was returned to room temperature and then water was added, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/ethyl acetate=5/1) to obtain 3.42 g of the title compound (yield: 94%).

Workup

  1. temperatureunder cooling in a dry ice-acetone bath over 30 minutes
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-efe98a18ead74742a89900f4fd627017
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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