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

HRID 323536
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 323536
[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]
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Komponenten

5

Edukt 3

HCID 5904Penicillin GHCID 14798Sodium HydroxideHCID 20644236Racemic ethyl 3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1061PhosphateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a134e06962504c938f001d697517685b
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06214609B1

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