Hydrochloric Acid → 1-(4-Cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)piperidine-4-carboxylic acid

HRID 17430ノート

反応式

HRID 17430 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2 回HCID 68584931Ethyl 1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}piperidine-4-carboxylate

生成物 1

HCID 685863861-(4-Cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)piperidine-4-carboxylic acid収率 73.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl 1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}piperidine-4-carboxylate (I-162) (0.26 g, 0.52 mmol) was dissolved in tetrahydrofuran (10 ml), then 1 N sodium hydroxide (0.60 ml, 0.60 mmol) was added. After stirring at room temperature for 19 hours, 1 N sodium hydroxide (0.40 ml, 0.40 mmol) was further added, followed by stirring at room temperature for 24 hours. 1 N Hydrochloric acid (1.00 ml, 1.00 mmol) was added, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol:water=8:3:0.5), then ethanol and a small amount of ether were added, and the insoluble matter was collected by filtration to obtain a colorless solid (0.18 g, 71%).

後処理

  1. stirringby stirring at room temperature for 24 hours
  2. customthe solvent was evaporated away under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol:water=8:3:0.5)
  4. additionethanol and a small amount of ether were added
  5. filtrationthe insoluble matter was collected by filtration

出典と根拠

ORDレコード
ord-517dcedeb4734de6a7071bc5b7709581
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…