Ethyl Acetate → HCID 10204776, compound

HRID 895889Notes

Reaction equation

HRID 895889 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:31])[N:25]([CH3:30])[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>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=1[C:6]([NH:5][C@H:4]([C:3]([OH:32])=[O:2])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24](=[O:31])[N:25]([CH3:30])[CH:26]=[C:27]([Cl:29])[CH:28]=2)=[CH:19][CH:18]=1)=[O:7]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 59912891HCID 59912891, compound

Product 1

HCID 10204776HCID 10204776, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine methyl ester (51 mg, 0.108 mmol) in THF (3 mL) was treated with a solution of lithium hydroxide monohydrate (18 mg, 0.43 mmol) in water (1.0 mL). Additional THF was added to effect a clear solution and the reaction mixture was stirred 1 hr. 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 N-[(2-chloro-6-methylphenyl)carbonyl]-4-(5-chloro-1-methyl-2-oxo-3-pyridinyl)-L-phenylalanine (40 mg, 82%) as a white solid. LR-Electrospray: m/z positive ion, 481(M+Na), 459(M+H (2 Cl)); negative ion, 457 (M−H (2 Cl)).

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-90cb0b302a9c4881961684f04799c241
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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