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

HRID 70029

Reaction equation

HRID 70029 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-47d325688989478f86a0ff635beffd20
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Linked notes

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