Hexylamine → HCID 131709883, compound

HRID 1579148Notes

Reaction equation

[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(OC(Cl)=O)C.[CH2:25]([NH2:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O1CCCC1>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH2:25]([NH-:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: -10 °C

Procedure

50 g (0.1 mol) of Z-Pro-OH were dissolved in 400 ml of anhydrous tetrahydrofuran, 28 ml of triethyl amide were added. The mixture was cooled to -10° and then 19.5 ml (0.2 mol) of chloroformic acid ethyl ester were added dropwise. After stirring for 10 minutes at -10°C, 96 ml (1 mol) of n-hexyl amine were added portionwise at this temperature, and the whole was stirred for another 6 hours without cooling. Subsequently it was evaporated under reduced pressure and taken up with ethyl acetate. The ethyl acetate solution was extracted with a 5 % KHSO4 -solution, saturated NaHCO3 -solution and water. After evaporating the ethyl acetate solution, dried over sodium sulfate, the product was crystallized.

Workup

temperatureThe mixture was cooled to -10°
stirringthe whole was stirred for another 6 hours
temperaturewithout cooling
customSubsequently it was evaporated under reduced pressure
extractionThe ethyl acetate solution was extracted with a 5 % KHSO4 -solution, saturated NaHCO3 -solution and water
customAfter evaporating the ethyl acetate solution
dry with materialdried over sodium sulfate
customthe product was crystallized

Sources & evidence

ORD record: ord-857b321736224bf1ba654097b97b986b
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03931139

Reaction notes

Loading…