Toluene → L-aspartyl-L-phenylalanine methyl ester hydrochloride dihydrate

HRID 1633385

Reaction equation

HRID 1633385 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:5][C:6](=[O:19])[C@H:7]([CH2:15][C:16](=[O:18])[OH:17])[NH:8]C(=O)CC(C)=O.C1(C)C=CC=CC=1.[ClH:35].N[OH:37]>O.C(O)(=O)C>[OH2:2].[OH2:37].[ClH:35].[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:5][C:6](=[O:19])[C@H:7]([CH2:15][C:16](=[O:17])[OH:18])[NH2:8]

Participants

6

Reactant 3

HCID 1140TolueneHCID 443297Hydroxyamine hydrochlorideHCID 13334676N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

Product 1

HCID 13020137L-aspartyl-L-phenylalanine methyl ester hydrochloride dihydrate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The crude N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester was dissolved in 100 parts by volume of water and 11.7 parts by volume of acetic acid. Toluene 200 parts by volume and 6.95 parts of hydroxylamine hydrochloride were added and the mixture stirred for 2.5 hours. The aqueous layer was separated and cooled to 0°-5° C. 15 parts by volume concentrated hydrochloric acid were added and the resulting mixture was cooled at 0°-5° C. overnight. The precipitate was collected on a filter and air dried for 3 hours to give 26.4 parts of α-L-aspartyl-L-phenylalanine methyl ester hydrochloride dihydrate.

Workup

  1. customThe aqueous layer was separated
  2. temperaturecooled to 0°-5° C
  3. addition15 parts by volume concentrated hydrochloric acid were added
  4. temperaturethe resulting mixture was cooled at 0°-5° C. overnight
  5. customThe precipitate was collected on
  6. filtrationa filter
  7. customair dried for 3 hours

Sources & evidence

ORD record
ord-b016a516852d4fdea7a33bbcaa231f3a
Source dataset
uspto-grants-1984_10
Patent number
US04480112

Linked notes

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