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

HRID 642302노트

반응식

HRID 642302 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 23694274Sodium methanolate methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d183f92d11194cd0afe4c8e0f487ea09
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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