Hydrochloric Acid → 4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride

HRID 895901Notes

Reaction equation

HRID 895901 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:27])[N:22]([CH3:26])[CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[ClH:29]>O1CCOCC1>[ClH:29].[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:27])[N:22]([CH3:26])[CH:23]=[CH:24][CH:25]=2)=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69715223N-[(1,1-dimethylethoxyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

Product 1

HCID 697153224-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[(1,1-dimethylethoxyl)carbonyl]-4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (60 mg, 0.155 mmol) in 4 N HCl in dioxane (4 mL) was stirred for 2 hr and was concentrated. The residue was triturated with several portions of ether to give 4-(1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride (55 mg, quant) as a white powder. LRMS-Electrospray: m/z positive ion 573 (2M+H) 328 (M+H+CH3CN) 319 (M+H+CH3OH) 287 (M+H). HRMS: Obs. Mass 287.1396. Calcd. Mass 287.1396 (M+H)

Workup

  1. concentrationwas concentrated
  2. customThe residue was triturated with several portions of ether

Sources & evidence

ORD record
ord-8f656cd8f4f24daebd59c53b5dcdb1a4
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

Loading…