Dicyclohexylcarbodiimide → HCID 13748635, compound

HRID 2164779Notes

Reaction equation

HRID 2164779 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:30]1([S:36][CH2:37][CH:38]([CH3:42])[C:39](O)=[O:40])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]([C:39](=[O:40])[CH:38]([CH3:42])[CH2:37][S:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12759329775-20-2HCID 13298943Tert-butyl 2-(cyclopentylamino)acetate

Product 1

HCID 13748635HCID 13748635, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold solution of 19.9 g (0.1M) of N-cyclopentyl glycine-t-butyl ester in 200 ml THF was added 26 g dicyclohexyl carbodiimide. After stirring for 1/2 hour, a solution of 19.6 g (0.1M) of 3-phenylthio-2-methyl propanoic acid in 50 ml THF was added and stirring continued for 16 hours. It was then filtered, solvent removed, dissolved in ether, washed well with water, filtered, dried over MgSO4, and evaporated to dryness leaving an oily residue which was purified by HPLC using ethyl acetate-hexane (3:17) as eluent.

Workup

  1. stirringstirring
  2. waitcontinued for 16 hours
  3. filtrationIt was then filtered
  4. customsolvent removed
  5. dissolutiondissolved in ether
  6. washwashed well with water
  7. filtrationfiltered
  8. dry with materialdried over MgSO4
  9. customevaporated to dryness
  10. customleaving an oily residue which
  11. customwas purified by HPLC

Sources & evidence

ORD record
ord-54cf299b1c0d454fb06cde1b2001f501
Source dataset
uspto-grants-1985_03
Patent number
US04507316

Reaction notes

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