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

HRID 642282ノート

反応式

HRID 642282 の反応式
C(O[C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[S:20][C:8]=2[C:7]=1[OH:27])=[O:5])C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31]>C[O-].[Na+].CO>[OH:27][C:7]1[C:8]2[S:20][C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:18][C:9]=2[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:11][C:6]=1[C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:5]

参加物

4

反応物 2

HCID 750GlycineHCID 684280397-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 24757066[(7-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid収率 96.6%

試薬・触媒・溶媒 1

HCID 23694274Sodium methanolate methanol溶媒

実験手順

A mixture of 7-hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (45 mg, 0.12 mmol) and glycine (179 mg, 2.38 mmol) in 0.5 M sodium methoxide/methanol (4.5 mL) was refluxed for four days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (20 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3 mL). The suspension was extracted with ethyl acetate (2×25 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (47 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.46 (t, 1H), 8.68 (m, 2H), 8.22 (m, 2H), 7.65 (m, 6H), 4.09 (m, 2H); MS: (+) m/z 406.0 (M+1)

後処理

  1. temperaturewas refluxed for four days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (20 mL)
  4. extractionextracted twice with dichloromethane
  5. extractionThe suspension was extracted with ethyl acetate (2×25 mL)
  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-5c4cd24530834db2928ddf469d5144d9
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

読み込み中…