Cyclopentylamine → HCID 53661661, 화합물

HRID 1448735노트

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HRID 1448735 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([NH2:45])[CH2:44][CH2:43][CH2:42][CH2:41]1>O1CCCC1>[CH:40]1([NH:45][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])[CH2:44][CH2:43][CH2:42][CH2:41]1

참가 물질

6

반응물 4

HCID 2906CyclopentylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 5388928Z-Ala Prolinal

생성물 1

HCID 53661661HCID 53661661, 화합물수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

6.4 g (0.02 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 100 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 2.54 ml of N-ethylmorpholine and 2.62 ml of isobutyl chloroformate were added and the mixture was stirred at -10° C. for 20 minutes. 1.98 ml of cyclopentylamine were then added and the mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. The mixture was then evaporated and the product which crystallised on the addition of water was extracted into ethyl acetate. The organic layer was washed neutral, dried over sodium sulphate and evaporated, the product crystallising on the addition of ether. There were obtained 4.8 g (71%) of N-benzyloxycarbonyl-L-alanyl-L-proline cyclopentylamide of melting point 118°-119° C.; [α]D20 =-93.5° (c=1.0228% in methanol).

후처리

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. customat room temperature
  3. customovernight
  4. customThe mixture was then evaporated
  5. customthe product which crystallised on the addition of water
  6. extractionwas extracted into ethyl acetate
  7. washThe organic layer was washed neutral
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customthe product crystallising on the addition of ether

출처 및 근거

ORD 기록
ord-df1843cdafce4748a778b69c1d6cbf80
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04187216

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