4-Methylmorpholine → HCID 67057155, compound

HRID 1866840Notes

Reaction equation

HRID 1866840 reaction equation
[CH3:1][C@H:2]([NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[C:3]([OH:5])=O.Cl.[NH2:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].CN1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:10]([O:9][C:7](=[O:8])[NH:6][CH:2]([C:3](=[O:5])[NH:18][CH2:19][C:20](=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 736104N-carbobenzyloxyalanineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67057155HCID 67057155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of commercially available N-α-CBZ-L-alanine (2.11 g, 9.5 mmol) in dichloromethane (50 mL) was added 2-aminoacetophenone hydrochloride (1.62 g, 9.5 mmol). The resulting solution was cooled to 0° C. and N-methylmorpholine (1.15 g, 11 mmol), 1-hydroxybenzotriazole (2.55 g, 18.9 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.35 g, 12.3 mmol), in that order, were added under an Argon atmosphere. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched by addition of saturated aqueous NaHCO3 solution; the separated organic phase was washed with 2N citric acid, saturated NaHCO3 solution and brine, then dried over MgSO4 overnight. After filtration and concentration, the residue was purified by column chromatography on silica gel (eluent, EtOAc:hexane-1:1) to yield the title compound, [1-(2-oxo-2-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid benzyl ester.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customThe reaction was quenched by addition of saturated aqueous NaHCO3 solution
  3. washthe separated organic phase was washed with 2N citric acid, saturated NaHCO3 solution and brine
  4. dry with materialdried over MgSO4 overnight
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by column chromatography on silica gel (eluent, EtOAc:hexane-1:1)

Sources & evidence

ORD record
ord-aa9adb76cc5945b8afbb93173e50e642
Source dataset
uspto-grants-2009_12
Patent number
US07629488B2

Reaction notes

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