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

HRID 642331노트

반응식

HRID 642331 반응식
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[C:9]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:17][C:8]=2[C:7]=1[OH:24])=[O:5])C.[NH2:25][CH2:26][C:27]([OH:29])=[O:28]>C[O-].[Na+].CO>[OH:24][C:7]1[C:8]2[S:17][C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:15][C:9]=2[C:10]([CH2:12][CH2:13][CH3:14])=[N:11][C:6]=1[C:4]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:5]

참가 물질

4

반응물 2

HCID 750GlycineHCID 684281827-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 24757244[(7-Hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid수율 81.9%

시약·촉매·용매 1

HCID 23694274Sodium methanolate methanol용매

실험 절차

A mixture of 7-hydroxy-2-phenyl-4-propyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (78 mg, 0.23 mmol) and glycine (343 mg, 4.57 mmol) in 0.5 M sodium methoxide/methanol (8.6 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (30 mL) and extracted three times with methyl t-butyl ether. The remaining aqueous layer was acidified to pH=3 with 1N HCl (6 mL). The solid precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (70 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.02 (br s, 1H), 9.21 (br s, 1H), 8.17 (m, 2H), 7.65 (m, 3H), 4.06 (d, J=6.2 Hz, 2H), 3.33 (m, 2H), 1.92 (m, 2H), 1.04 (t, J=7.0 Hz, 3H); MS: (+) m/z 371.93 (M+1).

후처리

  1. temperaturewas refluxed for three days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (30 mL)
  4. extractionextracted three times with methyl t-butyl ether
  5. filtrationThe solid precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-1a008bc6230942d283c7c8ed0ada0430
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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