Penicillin G → (S)-ethyl-3-(phenylacetamido)-4-pentynoic acid

HRID 323537

Reaction equation

HRID 323537 reaction equation
[CH2:1]([CH:3]([CH:7]([NH:10][C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]#[CH:9])[C:4]([OH:6])=[O:5])[CH3:2].[OH-].[Na+].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O>P([O-])([O-])([O-])=O>[CH2:1]([C@@H:3]([CH:7]([NH:10][C:11](=[O:19])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:8]#[CH:9])[C:4]([OH:6])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5904Penicillin GHCID 14798Sodium HydroxideHCID 53724360Racemic ethyl 3-(phenylacetamido)-4-pentynoic acid

Product 1

HCID 88221134(S)-ethyl-3-(phenylacetamido)-4-pentynoic acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Racemic ethyl 3-(phenylacetamido)-4-pentynoic acid (400 mg) was suspended in phosphate buffer (100 mL, 0.01 molar, prepared from 0.1 molar pH 7.24 solution obtained from sigma). The pH of the solution was adjusted between 8.0 to 8.2 using dilute sodium hydroxide. Under slow stirring, 100 units of immobilized penicillin G acylase (Boehringer-Mannheim) was added. The reaction mixture was stirred at room temperature for 48 hours, the pH was adjusted to 3.0, and then extracted with ethyl acetate (3×50 mL). The organic extracts were combined, dried over magnesium sulfate, filtered and evaporated to give the desired amide, (S)-ethyl-3-(phenylacetamido)-4-pentynoic acid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-196624977377444398f9d979a67cf12b
Source dataset
uspto-grants-2001_04
Patent number
US06214609B1

Linked notes

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