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

HRID 895911Notes

Reaction equation

HRID 895911 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=[CH:24][C:25]=2[CH3:26])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[ClH:30]>O1CCOCC1>[ClH:30].[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=[CH:24][C:25]=2[CH3:26])=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69715142N-[(1,1-dimethylethoxyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

Product 1

HCID 697162244-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride saltYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-[(1,1-dimethylethoxyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (132 mg, 0.33 mmol) in dioxane (1 mL) was added 4 N HCl solution in dioxane (1.5 mL) at room temperature. The solution was stirred for 4 h and concentrated under vacuum. The residue was dissolved in methanol (5 ml) and toluene (5 mL) and concentrated under vacuum to give 111 mg (99% yield) of 4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester hydrochloride salt as an amorphous white solid. EI-HRMS m/e calcd for C17H20N2O3 (M+) 300.1474. found 300.1486. e) Preparation of N-[(2,6-dichlorophenyl)carbonyl]-4-(1,4-dimethyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in methanol (5 ml)
  3. concentrationtoluene (5 mL) and concentrated under vacuum

Sources & evidence

ORD record
ord-9644fb323d4e4da6aa4eb04fc6bbe6d2
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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