Cyclooctylamine → HCID 53872165, 화합물

HRID 1448740노트

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HRID 1448740 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 53872165HCID 53872165, 화합물수율 59.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e51770d103fc40a3aaa67ba523f9db7c
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04187216

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