4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-N-[(1,l-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester → 4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester

HRID 895887Notes

Reaction equation

HRID 895887 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]=[C:24]([Cl:26])[CH:25]=2)=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O>Cl.O1CCOCC1>[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]=[C:24]([Cl:26])[CH:25]=2)=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 1

HCID 599128884-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-N-[(1,l-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 599128924-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl esterYield 87.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (210 mg, 0.50 mmol) in 4 N HCl in dioxane (10 mL) was stirred for 1 hr and was concentrated to give 4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (140 mg) as a white powder. LR(+)LSIMS: m/z 641 (2M+H), 321 (M+H).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-129151b9381a40118e2d3cba1121eae7
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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