Hydrochloric Acid → HCID 67200624, compound

HRID 551296Notes

Reaction equation

HRID 551296 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([NH:15]C(OC(C)(C)C)=O)[CH:5]([OH:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:24]>>[ClH:24].[NH2:15][CH:4]([CH:5]([OH:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:23])=[O:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67200575HCID 67200575, compound

Product 1

HCID 67200624HCID 67200624, compound

Procedure

Reaction was carried out in the same manner as in Example 27, except that 2.5 g of N-Boc-glycine methyl ester was used in place of 1-dimethylethyl-(2R)-(2,6-dichlorophenyl)-5-oxo-3-((1′R)-phenylethyl)tetrahydro-1H-1-imidazolecarboxylate to obtain 3.3 g of 2-(N-Boc-amino)-3-hydroxy-5-phenylpentanoic acid methyl ester as a white solid (yield: 78%). Further, 11.0 g of 2-(N-Boc-amino)-3-hydroxy-5-phenylpentanoic acid methyl ester was mixed with a 6 M hydrochloric acid, and the mixture was refluxed for 4 hours. Thereafter, the solvent was removed in reduced pressure to obtain 2-amino-3-hydroxy-5-phenylpentanoic acid hydrochloride. The retention time of the respective isomers was confirmed using the product. Further, the pH of the aqueous solution of the hydrochloride salt was adjusted to 6 to 7 by a 30% aqueous solution of sodium hydroxide to obtain 346 mg of 2-amino-3-hydroxy-5-phenylpentanoic acid as a white solid (yield: 53%).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThereafter, the solvent was removed in reduced pressure

Sources & evidence

ORD record
ord-6ff596b4a2d94792ab2e9d47dd7fd27d
Source dataset
uspto-grants-2011_05
Patent number
US07947722B2

Reaction notes

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