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Hydrochloric Acid → {[4-Cyano-7-hydroxy-3-(4-methoxy-phenyl)-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 2388215
ノート
印刷プレビュー

反応式

HRID 2388215 の反応式
[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:20])=[C:5]([C:21](OCC)=[O:22])[N:4]=1)#[N:2].[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].Cl>C(=O)(O)[O-].[Na+]>[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:20])=[C:5]([C:21]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:22])[N:4]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10942334Sodium MethoxideHCID 67530678Ethyl 4-cyano-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

生成物 1

HCID 42633241{[4-Cyano-7-hydroxy-3-(4-methoxy-phenyl)-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid収率 71.6%

試薬・触媒・溶媒 1

HCID 516892
Sodium Bicarbonate
溶媒

実験手順

Ethyl 4-cyano-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (86 mg, 0.254 mmol) and glycine (381 mg, 5.07 mmol) were added to sodium methoxide solution (7.6 mL, 3.80 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and 0.25 M hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 75 mg of crude solid. The solid was dissolved in 200 mL of saturated sodium bicarbonate solution and washed with EtOAc. The aqueous layer was acidified to pH 3 with concentrated hydrochloric acid and the precipitate was collected by filtration. The solid was dried under vacuum to afford 67 mg of the title compound. MS: (−) m/z 367.34 (M−1).

後処理

  1. temperaturethe mixture was refluxed for 3 days
  2. customThe precipitate was isolated by filtration
  3. customdried under vacuum
  4. customto give 75 mg of crude solid
  5. washwashed with EtOAc
  6. filtrationthe precipitate was collected by filtration
  7. customThe solid was dried under vacuum

出典と根拠

ORDレコード
ord-d67c48c49add4598ace66c61c529fc46
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08269008B2

反応ノート

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