Dicyclohexylcarbodiimide → HCID 14031642, compound

HRID 986613Notes

Reaction equation

HRID 986613 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:32]12(O)[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]3)[CH2:33]1)[CH2:39]2>C1COCC1.CN(C)C1C=CN=CC=1.CC(O)=O.CCOC(C)=O>[C:32]12([O:15][C:14](=[O:16])[C@@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]3)[CH2:33]1)[CH2:39]2

Participants

8

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 641521-AdamantanolHCID 70832N-Cbz-d-alanine

Product 1

HCID 14031642HCID 14031642, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-D-alanine (11.15 g, 50 mmol) was dissolved in 250 mL THF and treated with DCC (10.3 g, 50 mmol), 1-adamantanol (7.7 g, 51 mmol) and 1.45 g of 4-dimethylaminopyridine. The reaction mixture was stirred at room temperature. At the end of 24 hours, a few drops of HOAc was added and the reaction mixture was stirred for an additional 15 minutes. DCU was filtered off, the filtrate was evaporated to dryness under reduced pressure. The oily residue so obtained was dissolved in EtOAc and the solution was refrigerated overnight. More DCU was filtered off. The filtrate was then washed with 0.1N HCl (3×), H2O (3×), 0.1N NaOH (3×), H2O (3×) and dried over anhydrous Na2SO4. The solution was evaporated to dryness to give a clear oil. The oil was subjected to sublimation at 100°/0.1 mm for 5 hours. The oily residue was crystallized from hexane: mp 72°-74°, yield 11.6 g (75%), 250 MHz nmr (CDCl3, ppm) 1.37 (d, 3H, J=7.35 Hz, β--CH3 of Ala), 1.65 (s, 6H, adamantyl aliphatic protons of C's 4, 6 and 10), 2.09 (s, 6H, 1-adamantyl aliphatic protons of C's 2, 8 and 9), 2.16 (s, 3H, 1-adamantyl aliphatic protons of C's 3, 5 and 7), 4.23 (m, 1H, α--H of Ala), 5.09 (s, 2H, Ar--CH2 --O--), 5.32 (br.d, amide proton), 7.33 (s, 5H, ArH5).

Workup

  1. stirringthe reaction mixture was stirred for an additional 15 minutes
  2. filtrationDCU was filtered off
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe oily residue so obtained
  5. filtrationMore DCU was filtered off
  6. washThe filtrate was then washed with 0.1N HCl (3×), H2O (3×), 0.1N NaOH (3×), H2O (3×)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solution was evaporated to dryness
  9. customto give a clear oil
  10. customwas subjected to sublimation at 100°
  11. customfor 5 hours
  12. customThe oily residue was crystallized from hexane

Sources & evidence

ORD record
ord-6c8c00c266634ae7bad40d84d34a154d
Source dataset
uspto-grants-1987_12
Patent number
US04714619

Reaction notes

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