Cyclooctylamine → HCID 53872165, compound

HRID 1448740Notes

Reaction equation

HRID 1448740 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=O)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH:40]1([NH2:48])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>O1CCCC1>[CH:40]1([NH:48][C:18](=[O:20])[C@@H:17]2[CH2:21][CH2:22][CH2:23][N:16]2[C:14](=[O:15])[C@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 2903CyclooctylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 5388928Z-Ala Prolinal

Product 1

HCID 53872165HCID 53872165, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

6.4 g (0.02 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 75 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 2.54 ml (0.02 mol) of N-ethylmorpholine and 2.62 ml (0.02 mol) of isobutyl chloroformate were added and the resulting solution was stirred at -10° C. for 20 minutes. A solution of 2.5 g (0.02 mol) of cyclooctylamine in 25 ml of dry tetrahydrofuran was then added. The resulting mixture was stirred at 0° C. for 1 hour and then left to stand at room temperature for 16 hours. The tetrahydrofuran was removed by evaporation and the residue extracted with two 50 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed successively with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water and then dried over magnesium sulphate. Evaporation yielded an oil which solidified upon trituration with ether/petroleum ether. After recrystallisation from ethyl acetate/petroleum ether, there were obtained 5.1 g (59.3%) of N-benzyloxycarbonyl-L-alanyl-L-proline cyclooctylamide of melting point 94°-96° C.; [α]D20 =-95.0° (c=1.02% in methanol).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 hour
  2. waitleft
  3. waitto stand at room temperature for 16 hours
  4. customThe tetrahydrofuran was removed by evaporation
  5. extractionthe residue extracted with two 50 ml portions of ethyl acetate
  6. washThe combined ethyl acetate extracts were washed successively with 1-N hydrochloric acid, water, 5% sodium bicarbonate solution and water
  7. dry with materialdried over magnesium sulphate
  8. customEvaporation
  9. customyielded an oil which
  10. customAfter recrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e51770d103fc40a3aaa67ba523f9db7c
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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