Hydrochloric Acid → (S)-2-[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)amino]-propionic acid

HRID 2388170ノート

反応式

HRID 2388170 の反応式
[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([O:10]CC)=O.[NH2:22][C@H:23]([C:25]([OH:27])=[O:26])[CH3:24].[O-]CC.[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([NH:22][C@@H:23]([CH3:24])[C:25]([OH:27])=[O:26])=[O:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 2723922Sodium ethoxideHCID 67530168HCID 67530168、化合物

生成物 1

HCID 42635755(S)-2-[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)amino]-propionic acid収率 79.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Ethyl 7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (0.1 g, 0.35 mmol) was dissolved in 10 mL of DMF. L-Alanine (0.627 g, 7.04 mmol) and sodium ethoxide (0.36 g, 5.28 mmol) were added and the mixture was refluxed for 3 h. The mixture was cooled to room temperature and diluted with 70 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 2. The resulting suspension was filtered and the solid dried under vacuum to give 91 mg of the title compound. MS: (+) m/z 328.00 (M+1).

後処理

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationThe resulting suspension was filtered
  3. customthe solid dried under vacuum

出典と根拠

ORDレコード
ord-8f53663229d84adfa290d93211bbecc5
出典データセット
uspto-grants-2012_09
特許番号
US08269008B2

反応ノート

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