Methanol → 4-{[2-(Benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylic acid

HRID 1515350ノート

反応式

HRID 1515350 の反応式
[CH2:1]([O:8][C:9](=[O:26])[CH2:10][NH:11][CH:12]1[CH:19]2[CH2:20][C:15]3([C:22]([O:24]C)=[O:23])[CH2:16][CH:17]([CH2:21][CH:13]1[CH2:14]3)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:26])[CH2:10][NH:11][CH:12]1[CH:19]2[CH2:20][C:15]3([C:22]([OH:24])=[O:23])[CH2:16][CH:17]([CH2:21][CH:13]1[CH2:14]3)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68520083Methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate

生成物 1

HCID 685128294-{[2-(Benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate thus obtained (3.30 g) in tetrahydrofuran (20 ml), methanol (10 ml) and 8M aqueous sodium hydroxide (10 ml) were added and stirred at room temperature for 3 hours. After the reaction mixture was concentrated, the resulting residue was diluted with 1M aqueous sodium hydroxide and washed with diethyl ether. The resulting aqueous layer was diluted with 12M aqueous hydrochloric acid and extracted with chloroform. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure to give 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylic acid (2.95 g) as a light-brown viscous substance.

後処理

  1. concentrationAfter the reaction mixture was concentrated
  2. additionthe resulting residue was diluted with 1M aqueous sodium hydroxide
  3. washwashed with diethyl ether
  4. additionThe resulting aqueous layer was diluted with 12M aqueous hydrochloric acid
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter the desiccant was filtered off
  9. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-ebf1f60804e549be95aae619d1e3e15f
出典データセット
uspto-grants-2012_07
特許番号
US08222417B2

反応ノート

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