L-Alanine → HCID 68428367、化合物

HRID 642285ノート

反応式

HRID 642285 の反応式
C(O[C:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][C@H:24]([C:26]([OH:28])=[O:27])[CH3:25]>C[O-].[Na+].CO>[OH:22][C:7]1[C:8]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:13][C:9]=2[C:10]([CH3:12])=[N:11][C:6]=1[C:4]([NH:23][CH:24]([CH3:25])[C:26]([OH:28])=[O:27])=[O:5]

参加物

4

反応物 2

HCID 5950L-AlanineHCID 68426288HCID 68426288、化合物

生成物 1

HCID 68428367HCID 68428367、化合物収率 38.5%

試薬・触媒・溶媒 1

HCID 23694274Sodium methanolate methanol溶媒

反応条件

温度
120 °C

実験手順

A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (50 mg, 0.16 mmol) and L-alanine (146 mg, 1.63 mmol) in 0.5 M sodium methoxide/methanol (2.6 mL) was heated at 120° C. in a microwave vessel for 3 h before it was cooled to room temperature and concentrated in vacuo. Water was added to the residue and extracted four times with dichloromethane until no UV spot in the dichloromethane layer. The remaining aqueous layer was acidified to pH=3 with 1N HCl (2 mL). The suspension was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound as a white solid (22 mg): 1H NMR (DMSO-d6, 200 MHz): δ=12.98 (br s, 1H), 9.06 (d, J=7.4 Hz, 1H), 8.15 (m, 2H), 7.61 (m, 3H), 4.54 (m, 1H), 2.88 (s, 3H), 1.49 (d, J=7.4 Hz, 3H); MS: (+) m/z 358.04 (M+1).

後処理

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionWater was added to the residue
  4. extractionextracted four times with dichloromethane until no UV spot in the dichloromethane layer
  5. extractionThe suspension was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-17aeb23ba8774985a75257876539bcb1
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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