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

HRID 1515350Notes

Reaction equation

HRID 1515350 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ebf1f60804e549be95aae619d1e3e15f
Source dataset
uspto-grants-2012_07
Patent number
US08222417B2

Reaction notes

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