Amantadine → HCID 86741458, compound

HRID 543249Notes

Reaction equation

HRID 543249 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7](O)=[O:8].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[C:24]12([NH2:34])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>CC(C)=O>[C:24]12([N:34]3[C:7](=[O:8])[CH2:2][CH2:3][C@H:4]3[C:5]([NH2:1])=[O:6])[CH2:31][CH:30]3[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]3)[CH2:25]1)[CH2:33]2

Participants

6

Reactant 4

HCID 2130AmantadineHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 86741458HCID 86741458, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g of (L)-pyroglutamic acid (77 mmol) and 10.7 ml of triethylamine are mixed with 100 ml of anhydrous acetone, 9.29 g of pivaloyl chloride (77 mmol) are run in slowly at -5° and then, after 15 minutes at 0° C., 11.65 g (77 mmol) of adamantanamine are added in several portions.

Workup

  1. customslowly at -5°

Sources & evidence

ORD record
ord-cb5f284428f141e4b57c51f89a71caba
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

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