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

HRID 323537

反応式

HRID 323537 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1061Phosphate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-196624977377444398f9d979a67cf12b
出典データセット
uspto-grants-2001_04
特許番号
US06214609B1

関連ノート

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