Ethyl Acetate → HCID 10230416, compound

HRID 895896Notes

Reaction equation

HRID 895896 reaction equation
C[O:2][C:3](=[O:38])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:37])[N:25]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:26]=[C:27]([Cl:29])[CH:28]=2)=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])=[O:7].O.[OH-].[Li+].C(OCC)(=O)C>C1COCC1.O>[CH2:30]([N:25]1[CH:26]=[C:27]([Cl:29])[CH:28]=[C:23]([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C@@H:4]([C:3]([OH:38])=[O:2])[NH:5][C:6]([C:8]3[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=3[Cl:15])=[O:7])=[CH:22][CH:21]=2)[C:24]1=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 69714729HCID 69714729, compound

Product 1

HCID 10230416HCID 10230416, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1-benzyl-5-chloro-2-oxo-pyridinyl)-L-phenylalanine methyl ester (72 mg, 0.13 mmol) in THF (3 mL) was treated with a solution of lithium hydroxide monohydrate (22 mg, 0.52 mmol) in water (1.0 mL). Additional THF was added to effect a clear solution and the reaction mixture was stirred 1.5 hr at which time, TLC (ethyl acetate) indicated starting material was consumed. A few drops of acetic were added and the entire reaction mixture was applied to a 4×30 cm, C-18 reversed phase HPLC column and eluted with a linear gradient of acetonitrile in water of 5 to 95% over 35 min. The product containing fraction was lyophillyzed to give 4-(1-benzyl-5-chloro-2-oxo-3-pyridinyl)-N-[(2-chloro-6-methylphenyl)carbonyl]-L-phenylalanine (50 mg, 71%) as a white solid. LR-Electrospray: m/z negative ion 533 (M−H (2 Cl)); positive ion 557(M+Na), 552 (M+NH4), 535 (M+H (2 Cl)). HRMS: Obs. Mass 535.1190. Calcd. Mass 535.1191 (M+H).

Workup

  1. customwas consumed
  2. additionA few drops of acetic were added
  3. customthe entire reaction mixture
  4. washeluted with a linear gradient of acetonitrile in water of 5 to 95% over 35 min
  5. additionThe product containing fraction

Sources & evidence

ORD record
ord-95b89431c5ec479a82fa55c28388ee00
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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