Phosphate → 2-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

HRID 70029

Reaktionsgleichung

Reaktionsgleichung von HRID 70029
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H:10]([C:13]([OH:15])=[O:14])[CH2:11][SH:12].P([O-])([O-])([O-])=O>CO>[C:2]1([C:1]2[S:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1061PhosphateHCID 5862L-(+)-CysteineHCID 7505Benzonitrile

Produkt 1

HCID 883272-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Benzonitrile (40 mmol) was combined with L-cysteine (45 mmol) in 100 mL of 1:1 MeOH/pH 6.4 phosphate buffer solution. The reaction was stirred at 40° C. for 3 days. The precipitate was removed by filtration, and MeOH was removed using rotary evaporation. To the remaining solution was added 1M HCl to adjust to pH=2 under 0° C. The resulting precipitate was filtered to yield a white solid 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid 42a, which was used directly to next step without purification.

Aufarbeitung

  1. customThe precipitate was removed by filtration, and MeOH
  2. customwas removed
  3. customevaporation
  4. additionTo the remaining solution was added 1M HCl
  5. customto adjust to pH=2 under 0° C
  6. filtrationThe resulting precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-47d325688989478f86a0ff635beffd20
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822513B2

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