Methylamine → N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester

HRID 1601934Notes

Reaction equation

HRID 1601934 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:20])[C@@H:9]([C:17](O)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:23]1[C:27]2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN>CN(C)C=O.CO.O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([CH3:20])[C@@H:9]([C:17](=[O:18])[NH:23][CH3:27])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7015127N-Boc-N-methyl-D-phenylalanine

Product 1

HCID 10613603N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl esterYield 108%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-Tert-butoxycarbonyl-N-methyl-D-phenylalanine (1.22 g, 4.4 mmol), 1-hydroxybenzotriazole hydrate (0.59 g, 4.4 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimid hydrochloride (0.88 g, 4.6 mmol) were dissolved in N,N-dimethylformamide (25 mL) and stirred for 30 min. Methylamine (0.51 g of a 40% solution in methanol, 6.6 mmol) was added and the mixture was stirred overnight. Methylene chloride (80 mL) and water (100 mL) were added and the phases were separated. The organic phase was washed with sodium hydroxide (20 mL, 1 N), sodium hydrogensulfate (50 mL, 10%) and water (50 mL). The organic phase was dried (magnesium sulfate) and the solvent removed in vacuo to afford 1.39 g of N-methyl-N-((R)1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester.

Workup

  1. stirringthe mixture was stirred overnight
  2. customthe phases were separated
  3. washThe organic phase was washed with sodium hydroxide (20 mL, 1 N), sodium hydrogensulfate (50 mL, 10%) and water (50 mL)
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eeffd029ce7644cca919626b9b58e719
Source dataset
uspto-grants-1999_11
Patent number
US05977178

Reaction notes

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