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

HRID 642289ノート

反応式

HRID 642289 の反応式
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:25])=[O:5])C.[NH2:26][CH2:27][C:28]([OH:30])=[O:29]>C[O-].[Na+].CO>[OH:25][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:5]

参加物

4

反応物 2

HCID 750GlycineHCID 684264227-Hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 68426552{[7-Hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid収率 77.8%

試薬・触媒・溶媒 1

HCID 23694274Sodium methanolate methanol溶媒

実験手順

A mixture of 7-hydroxy-2-(4-trifluoromethyl-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (40 mg, 0.11 mmol) and glycine (162 mg, 2.16 mmol) in 0.5 M sodium methoxide/methanol (4.1 mL) was refluxed for four days before it was cooled to room temperature and concentrated in vacuo. Water (20 mL) and 1N HCl (1.5 mL) was added and the mixture was extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (1.5 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 yellow solid (34 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.48 (br s, 1H), 8.94 (s, 1H), 8.35 (d, 2H), 7.96 (d, 2H), 4.03 (d, J=5.8 Hz, 2H); MS: (+) m/z 329.9 (M+1)

後処理

  1. temperaturewas refluxed for four days before it
  2. concentrationconcentrated in vacuo
  3. additionWater (20 mL) and 1N HCl (1.5 mL) was added
  4. extractionthe mixture was extracted twice with dichloromethane
  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-418b84ef259b44dca9574f0a0e4c88c8
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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