Amantadine → HCID 22816336, compound

HRID 1680580Notes

Reaction equation

C(OC(Cl)=O)C(C)C.[C:9]([NH:16][C@H:17]([C:25]([OH:27])=O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CN1CCOCC1.[NH2:35][C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([CH2:39]3)[CH2:37]1)[CH2:43]2>C(Cl)Cl>[C:9]([NH:16][C@H:17]([C:25]([CH:37]1[CH:38]2[CH2:39][CH:40]3[CH2:41][CH:42]([CH2:43][C:36]1([NH2:35])[CH2:45]3)[CH2:44]2)=[O:27])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

Conditions

Temperature: -10 °C

Procedure

Under a nitrogen atmosphere 6.5 ml of isobutylchloroformate is added to 100 ml of a stirred methylene chloride solution containing 2 g of 5A sieves, 13.26 g Boc-phenylalanine, and 5.5 ml of N-methylmorpholine at -50° C. Over a 30 minute period the reaction mixture is warmed to -10° C. and then recooled to -40° C., and 7.94 g of 1-aminoadamantane is added. The cooling bath is removed, and the reaction mixture is stirred at room temperature overnight. The solution is filtered and washed with 50 ml of cold 1 M potassium bisulfate solution followed by washes with 20 ml portions of 2 M potassium carbonate solution and saturated sodium chloride solution. The solution is then dried over sodium sulfate, filtered and concentrated to dryness to give Boc-L-phenylalanyl-1-aminoadamantane which is represented by the following formula ##STR32##

Workup

customrecooled to -40° C.
customThe cooling bath is removed
filtrationThe solution is filtered
washwashed with 50 ml of cold 1 M potassium bisulfate solution
dry with materialThe solution is then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-b768fb85d53241a7b255f859512c99f9
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04273704

Reaction notes

Loading…