Methylamine → ((1S)-1-Methylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

HRID 1872908Notes

Reaction equation

HRID 1872908 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.O[N:23]1[C:27]2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:27][NH:23][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 7201346((1S)-1-Methylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl esterYield 86.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-t-Butoxycarbonyl-L-phenylalanine (2.65 g, 10.0 mmol) was dissolved in N,N-dimethylformamide (20 ml). To the solution were added a 40% aqueous solution (0.8 ml, 10.3 mmol) of methylamine, 1-hydroxybenzotriazole (1.48 g, 11.0 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12.0 mmol) under cooling with ice water. The mixture was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate, washed twice with water and each once with a 10% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. After the desiccant was separated by filtration, the solvent was distilled off under reduced pressure. The resultant solids were washed with diisopropyl ether to obtain 2.41 g of the title compound.

Workup

  1. washwashed twice with water
  2. dry with materialeach once with a 10% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate
  3. customAfter the desiccant was separated by filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. washThe resultant solids were washed with diisopropyl ether

Sources & evidence

ORD record
ord-9133a75747f24e9b847db96cd410799d
Source dataset
uspto-grants-2000_08
Patent number
US06110967

Reaction notes

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