Water → HCID 86595212, compound

HRID 1793937Notes

Reaction equation

HRID 1793937 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:13][C:14](=[O:20])OC(C)(C)C.N1[CH:26]=[CH:25][CH:24]=CC=1.Cl[C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].[OH2:35].Cl[CH2:37]Cl>C(OCC)(=O)C>[C:25]([O:35][CH:12]([N:13]=[C:14]=[O:20])[CH2:11][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:9])[CH3:10])=[CH:7][C:2]=1[NH:1][C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH3:24])([CH3:26])[CH3:37]

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 20884Ethoxalyl chlorideHCID 86595210HCID 86595210, compound

Product 1

HCID 86595212HCID 86595212, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 0.15 g of tert-butyl [2-(2-amino-4-isopropylphenyl)ethyl]carbamate and 0.087 mL of pyridine in 2 mL of dichloromethane was added 0.072 mL of ethyl chlorooxoacetate under ice-cooling, and the mixture was stirred at room temperature for 4 hours. To the reaction mixture were added water and ethyl acetate, and the mixture was separated. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined. After being washed with water and brine successively, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.23 g of ethyl [2-(2-tert-butoxy-carbonylaminoethyl)-5-isopropylphenyl]oxalamate.

Workup

  1. temperaturecooling
  2. customthe mixture was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washAfter being washed with water and brine successively
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b66203e659eb4ed3b06beb1dd05dce72
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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