Cyclopentylamine → HCID 53661661、化合物

HRID 1448735ノート

反応式

HRID 1448735 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 53661661HCID 53661661、化合物収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-df1843cdafce4748a778b69c1d6cbf80
出典データセット
uspto-grants-1980_02
特許番号
US04187216

反応ノート

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