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

HRID 63202

反応式

HRID 63202 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6548f0433bdd4c3c9ebe2ed0cfadbf32
出典データセット
uspto-grants-2016_09
特許番号
US09447049B2

関連ノート

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