Hydrochloric Acid → HCID 86741119, compound

HRID 1731973Notes

Reaction equation

HRID 1731973 reaction equation
[CH2:1]([NH:5][C:6](=[O:38])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:37])[C@H:13]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[NH:14][C:15](OC(C)(C)C)=[O:16])[CH:2]([CH3:4])[CH3:3].Cl.C(N1CCOCC1)C.[C:48]12([CH2:58]C(Cl)=O)[CH2:57][CH:52]3[CH2:53][CH:54]([CH2:56][CH:50]([CH2:51]3)[CH2:49]1)[CH2:55]2>C(OCC)(=O)C>[CH2:1]([NH:5][C:6](=[O:38])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:37])[C@H:13]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[NH:14][C:15](=[O:16])[CH2:58][C:48]12[CH2:57][CH:52]3[CH2:51][CH:50]([CH2:56][CH:54]([CH2:53]3)[CH2:55]1)[CH2:49]2)[CH:2]([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 27718821-Adamantaneacetyl chlorideHCID 86741120HCID 86741120, compound

Product 1

HCID 86741119HCID 86741119, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2.72 g (0.005 mol) of Nα -tert.butoxycarbonyl-Nε -benzyloxycarbonyl-L-lysyl-L-proline isobutylamide were treated with 15 ml of 2.5M hydrogen chloride in ethyl acetate at room temperature for 0.75 hour. The solvent was removed by evaporation and the solid was washed with diethyl ether. The solid was taken up in 15 ml of dimethylformamide and the solution was cooled to 0° C. 1.27 ml (0.01 mol) of N-ethylmorpholine and 1.3 g (0.006 mol) of 1-adamantaneacetyl chloride were added and the mixture was stirred at room temperature for 3 hours. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate/water. The organic solution was washed with 5% citric acid solution, water, 5% sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated. Chromatography on 60 g of silica gel using ethyl acetate for the elution yielded 0.9 g (29%) of Nα -(1-adamantaneacetyl)-Nε -benzyloxycarbonyl-L-lysyl-L-proline isobutylamide as an oil.

Workup

  1. customThe solvent was removed by evaporation
  2. washthe solid was washed with diethyl ether
  3. customThe solvent was removed by evaporation
  4. dissolutionthe residue was dissolved in ethyl acetate/water
  5. washThe organic solution was washed with 5% citric acid solution, water, 5% sodium bicarbonate solution and brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. washfor the elution

Sources & evidence

ORD record
ord-9732af847a144e2e8875e8de634cafe8
Source dataset
uspto-grants-1986_11
Patent number
US04623639

Reaction notes

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