Water → N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1464224Notes

Reaction equation

HRID 1464224 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+].O>C(O)(=O)C>[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

6

Reactant 4

HCID 962WaterHCID 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 1

HCID 176Acetic AcidSolvent

Procedure

To 24.9 g (0.1 mole) of N-benzyloxycarbonyl-L-aspartic acid anhydride in 100.4 g of acetic acid were added 21.6 g (0.1 mole) of L-phenylalanine methyl ester hydrochloride and 7.6 g (0.055 mole) of potassium carbonate. The reaction was carried out for 3 hours with stirring at 15°-20.C. Thereafter 75.3 g of water was added and the mixture was stirred for one hour at 15°-20.C. The precipitated crystals were filtered, washed and dried to obtain crystals of N-benzyloxycarbonyl-α-L-aspartyl-phenylalanine methyl ester. Analysis of HPLC revealed that the crystals had an α-isomer:β-isomer ratio of 99.6:0.4. The yield of the α-isomer was 28.6 g. In the filtrate, 7.2 g of the α-isomer and 6.2 g of the β-isomer were present.

Workup

  1. filtrationThe precipitated crystals were filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-1028780f10d8443ab08f94d1dcff0370
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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