Penicillin G → (S)-ethyl-3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate

HRID 323536

Reaction equation

HRID 323536 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C@H:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[CH3:18]

Participants

5

Reactant 3

HCID 5904Penicillin GHCID 14798Sodium HydroxideHCID 20644236HCID 20644236, compound

Product 1

HCID 54332815(S)-ethyl-3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Racemic ethyl 3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate (1g) was suspended in phosphate buffer (250 mL, 0.01 molar, prepared from 0.1 molar pH 7.24 solution obtained from sigma). The pH of the solution was adjusted 7.8 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 reaction mixture was extracted with ethyl acetate (75 mL×3). The organic extracts were combined, dried over sodium sulfate, filtered and evaporated to dryness to give the desired amide, (S)-ethyl-3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate. The immobilized enzyme was filtered off from the aqueous phase using Whatman No.1 filter paper. The pH of the aqueous phase was adjusted to 8.0 using dilute sodium hydroxide, and extracted with ethyl acetate (75 mL×3). The extracts were combined, dried over sodium sulfate, filtered and evaporated to dryness to give the desired amine, (R)-ethyl-3-amino-5-(trimethylsilyl)-4-pentynoate.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (75 mL×3)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a134e06962504c938f001d697517685b
Source dataset
uspto-grants-2001_04
Patent number
US06214609B1

Linked notes

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