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

HRID 522561

Reaction equation

HRID 522561 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-d1f8f8b34afc4e7ebd9d47ee9e4269c0
Source dataset
uspto-grants-2016_05
Patent number
US09334242B2

Linked notes

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