HCID 69716734, compound → HCID 69715407, compound

HRID 895894Notes

Reaction equation

HRID 895894 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH2:13][C:14]1(CC2C=CC=CC=2)[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:27])[NH:22][CH:23]=[C:24]([Cl:26])[CH:25]=2)=[CH:16][CH2:15]1)[NH:5]C(OC(C)(C)C)=O>Cl.O1CCOCC1>[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:27])[N:22]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:23]=[C:24]([Cl:26])[CH:25]=2)=[CH:18][CH:19]=1)[NH2:5]

Participants

4

Reactant 1

HCID 69716734HCID 69716734, compound

Product 1

HCID 69715407HCID 69715407, compoundYield 203.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-benzyl-4-(5-chloro-2-oxo-3-pyridinyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (248 mg, 0.50 mmol) in 4 N HCl in dioxane (10 mL) was stirred for 1 hr and was concentrated. The residue was triturated with ether (15 mL) and was filtered to give 4-(1-benzyl-5-chloro-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (202 mg, 94%) as a white powder. LR-Electrospray: m/z 1015 (2M+Na, 4 Cl), 519 (M+Na) 514 (M+NH4), 497 (M+H). HRMS: Obs. Mass 496.1774. Calcd. Mass 496.1765 (M+H).

Workup

  1. concentrationwas concentrated
  2. customThe residue was triturated with ether (15 mL)
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-34b19bca74e449c59f8ea690a2149680
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

Loading…