Glycine → HCID 24757067、化合物

HRID 642284ノート

反応式

HRID 642284 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][CH2:24][C:25]([OH:27])=[O:26]>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][CH2:24][C:25]([OH:27])=[O:26])=[O:5]

参加物

4

反応物 2

HCID 750GlycineHCID 68426288HCID 68426288、化合物

生成物 1

HCID 24757067HCID 24757067、化合物収率 72.5%

試薬・触媒・溶媒 1

HCID 23694274Sodium methanolate methanol溶媒

実験手順

A mixture of 7-hydroxy-4-methyl-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (159 mg, 0.51 mmol) and glycine (760 mg, 1.01 mmol) in 0.5 M sodium methoxide/methanol (19.2 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (50 mL) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (12 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (127 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.01 (br s, 1H), 9.24 (br s, 1H), 8.14 (m, 2H), 7.62 (m, 3H), 4.03 (d, J=6.2 Hz, 2H), 2.87 (s, 3H); MS: (+) m/z 344.0 (M+1)

後処理

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 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-b6f439e8868e4274997e063fde0b159f
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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