Hydrochloric Acid → HCID 69331765, compound

HRID 1765986Notes

Reaction equation

HRID 1765986 reaction equation
C([NH:4][C@@H:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=1)(=O)C.C1(C)C=CC=CC=1.[ClH:26]>>[ClH:26].[CH3:15][O:14][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[CH3:13])[CH2:6][C@H:5]([C:16]([OH:18])=[O:17])[NH2:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 54030461HCID 54030461, compound

Product 1

HCID 69331765HCID 69331765, compound

Procedure

A mixture of N-acetyl-3-methoxy-4-methyl-D-phenylalanine (2.55 g) in a mixture of 6N hydrochloric acid (25.5 ml) with toluene (18 ml) was stirred under reflux for 4 hours. After cooling to room temperature, the aqueous layer was separated and the organic layer was washed twice with water (10 ml). The aqueous layer and the washings were combined and the solvent was evaporated under reduced pressure. The produced crystals were collected by filtration and washed with ice-water to give 3-methoxy-4-methyl-D-phenylalanine hydrochloride (1.35 g) in the form of colorless crystals. The solvent was evaporated from the filtrate under reduced pressure to give crude 3-methoxy-4-methyl-D-phenylalanine hydrochloride (0.6 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe aqueous layer was separated
  3. washthe organic layer was washed twice with water (10 ml)
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationThe produced crystals were collected by filtration
  6. washwashed with ice-water

Sources & evidence

ORD record
ord-0a834d6d19f44ad59a49cf9c800f5927
Source dataset
uspto-grants-2007_06
Patent number
US07229992B2

Reaction notes

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