Methyl L-phenylalaninate hydrochloride → 33605-76-4

HRID 1464214Notes

Reaction equation

HRID 1464214 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:9](=[O:10])[O:8][C:6](=[O:7])[CH2:5]1)=[O:2].C([O-])(=O)C.[Na+].Cl.[CH3:17][O:18][C:19](=[O:29])[C@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH2:21]>C(O)(=O)C>[CH3:17][O:18][C:19](=[O:29])[C@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:21][C:9](=[O:10])[C@H:4]([CH2:5][C:6](=[O:7])[OH:8])[NH:3][CH:1]=[O:2]

Participants

5

Reactant 3

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 517045Sodium AcetateHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 1026805633605-76-4

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 28.6 g of acetic acid, 14.3 g (0.1 mole) of N-formyl-L aspartic anhydride was suspended and 9.2 g (0.11 mole) of sodium acetate was added with stirring at 5°-10° C. Successively 21.6 g (0.1 mole) of L-phenylalanine methylester hydrochloride was added and the reaction was carried out for 5 hours with stirring at the same temperature. The reaction mixture was then concentrated and 57.2 g of water was added. Precipitated crystals were filtered, washed and dried. Crystals of N-formyl-α-L-aspartyl-L-phenylalanine methyl ester thus obtained were 30.6 g.

Workup

  1. stirringwith stirring at the same temperature
  2. concentrationThe reaction mixture was then concentrated
  3. addition57.2 g of water was added
  4. customPrecipitated crystals
  5. filtrationwere filtered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-66aad48a707849d996c2ae31d1700ef8
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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