Benzyl chloroformate → 2-{[(Benzyloxy)carbonyl]amino}adamantane-2-carboxylic acid

HRID 582794Notes

Reaction equation

HRID 582794 reaction equation
[NH2:1][C:2]1([C:12]([OH:14])=[O:13])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[CH2:27]([O:34][C:35](Cl)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([O:34][C:35]([NH:1][C:2]1([C:12]([OH:14])=[O:13])[CH:9]2[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]1[CH2:11]3)[CH2:10]2)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 643542-Aminoadamantane-2-carboxylic acidHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 221118642-{[(Benzyloxy)carbonyl]amino}adamantane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

1.015 g of 2-amino-2-adamantanecarboxylic acid and 6 ml of bis(trimethylsilyl)acetamide in 10 ml of DCM is heated to reflux for one and a half hours. 0.75 ml of benzyloxycarbonyl chloride is added and the mixture is heated at 50° C. for 15 minutes. The reaction medium is cooled to -70° C., decomposition is then effected by adding ice and the mixture is extracted with AcOEt. The organic phase is washed with water (twice) and with brine, dried over MgSO4 and evaporated under vacuum. The product crystallizes in hexane; 1.164 g are obtained.

Workup

  1. temperatureto reflux for one and a half hours
  2. temperatureThe reaction medium is cooled to -70° C.
  3. additionby adding ice
  4. extractionthe mixture is extracted with AcOEt
  5. washThe organic phase is washed with water (twice) and with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under vacuum
  8. customThe product crystallizes in hexane
  9. custom1.164 g are obtained

Sources & evidence

ORD record
ord-ab6aa8bba20b4564af53528c2da65ace
Source dataset
uspto-grants-1999_07
Patent number
US05925661

Reaction notes

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