Hydrochloric Acid → (1-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)acetic Acid

HRID 17480ノート

反応式

HRID 17480 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([CH2:16][C:17]([O:19]CC)=[O:18])[CH2:13]3)[O:11][C:7]=2[C:6]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]2)=[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]=1[CH3:36])#[N:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([CH2:16][C:17]([OH:19])=[O:18])[CH2:13]3)[O:11][C:7]=2[C:6]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]2)=[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]=1[CH3:36])#[N:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86630853HCID 86630853、化合物

生成物 1

HCID 68584433(1-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)acetic Acid収率 17%

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}azetidin-3-yl)acetate (I-191) (220 mg, 0.45 mmol) was dissolved in tetrahydrofuran (5 ml), then 1 N sodium hydroxide (4.5 ml, 4.5 mmol) was added, followed by stirring at room temperature for 18 hours. After the reaction, the solvent was evaporated away under reduced pressure, then 1 N hydrochloric acid (4.5 ml, 4.5 mmol) was added, followed by extraction with a mixed solvent of chloroform:methanol (10:1) and by washing with saturated sodium hydrogencarbonate solution, then the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (4:1, v/v) gave the entitled compound (35 mg, 17%) as a pale yellow crystal.

後処理

  1. customAfter the reaction
  2. customthe solvent was evaporated away under reduced pressure
  3. extractionfollowed by extraction with a mixed solvent of chloroform:methanol (10:1)
  4. washby washing with saturated sodium hydrogencarbonate solution
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure

出典と根拠

ORDレコード
ord-1ec25370eb004dbea18ad7260458b590
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…