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

HRID 642302ノート

反応式

HRID 642302 の反応式
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH3:13])[C:9]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:16][C:8]=2[C:7]=1[OH:23])=[O:5])C.[NH2:24][CH2:25][C:26]([OH:28])=[O:27]>C[O-].[Na+].CO>[CH2:12]([C:10]1[C:9]2[N:14]=[C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:16][C:8]=2[C:7]([OH:23])=[C:6]([C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5])[N:11]=1)[CH3:13]

参加物

4

反応物 2

HCID 750GlycineHCID 684277474-Ethyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 24757157[(4-Ethyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid収率 82.3%

試薬・触媒・溶媒 1

HCID 23694274Sodium methanolate methanol溶媒

実験手順

A mixture of 4-ethyl-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (57 mg, 0.17 mmol) and glycine (259 mg, 3.45 mmol) in 0.5 M sodium methoxide/methanol (6.5 mL) was refluxed for 21 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (10 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (5 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (50 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.04 (br s, 1H), 9.22 (br s, 1H), 8.17 (m, 2H), 7.64 (m, 3H), 4.05 (d, J=6.2 Hz, 2H), 3.28 (q, J=7.8 Hz, 2H), 1.42 (t, J=7.8 Hz, 3H); MS: (+) m/z 357.97 (M+1), (−) m/z 355.95 (M−1).

後処理

  1. temperaturewas refluxed for 21 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (10 mL)
  4. extractionextracted twice with dichloromethane
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-d183f92d11194cd0afe4c8e0f487ea09
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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