Acetic Acid → N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1464225Notes

Reaction equation

HRID 1464225 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:17](=[O:18])[O:16][C:14](=[O:15])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][O:21][C:22](=[O:32])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:24].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>C(OCC)(=O)C.O>[CH3:20][O:21][C:22](=[O:32])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:24][C:17](=[O:18])[C@H:12]([CH2:13][C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Product 1

HCID 10159630N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 24.9 g (0.1 mole) of N-benzyloxycarbonyl-L-aspartic acid anhydride in 100.4 g of ethyl acetate were added 21.6 g (0.1 mole) of L-phenylalanine methyl ester hydrochloride and 7.6 g (0.055 mole) of potassium carbonate dissolved in 9.3 g of water. The reaction was carried out for 3 hours with stirring at 15°-20 C. Thereafter, 100.4 g of acetic acid and 75.3 g of water was added to the concentrate and the mixture was stirred for one hour at 15°-20.C. Precipitated crystals were filtered, washed and dried to obtain crystals of N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester.

Workup

  1. concentrationconcentrate
  2. stirringthe mixture was stirred for one hour at 15°-20.C
  3. customPrecipitated crystals
  4. filtrationwere filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-665769b7af8c4b4d85ded6fdd008b97c
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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