Cyclopentylamine → HCID 53661661, compound

HRID 1448735Notes

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([NH2:45])[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

Participants

Conditions

Temperature: -10 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-df1843cdafce4748a778b69c1d6cbf80
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04187216

Reaction notes

Loading…