Glycine → [(7-Hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642317ノート

反応式

HRID 642317 の反応式
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[S:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:14][C:8]=2[C:7]=1[OH:21])=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25]>C[O-].[Na+].CO>[OH:21][C:7]1[C:8]2[N:14]=[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5]

参加物

4

反応物 2

HCID 750GlycineHCID 684268667-Hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 24757161[(7-Hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid収率 75.9%

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-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (31 mg, 0.10 mmol) and glycine (78 mg, 1.04 mmol) in 0.5 M sodium methoxide/methanol (1.7 mL) was heated at 120° C. using a CEM microwave reactor for 30 min before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (18 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (1.2 mL). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (25 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.30 (br s, 1H), 9.42 (t, 1H), 8.96 (s, 1H), 8.14 (m, 2H), 7.67 (m, 3H), 4.02 (d, J=6.2 Hz, 2H); MS: (+) m/z 330.0 (M+1).

後処理

  1. customfor 30 min
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water (18 mL)
  5. extractionextracted twice with dichloromethane
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-ad8ca9e41fd047c5bb36afebf9557fcb
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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