Reaction #630431

ord-cb5f284428f141e4b57c51f89a71caba

Reaction equation

NC12CC3CC(CC(C3)C1)C2
adamantanamine
O=C1CC[C@@H](C(=O)O)N1
(L)-pyroglutamic acid
CCN(CC)CC
triethylamine
CC(C)(C)C(=O)Cl
pivaloyl chloride
→
NC(=O)[C@@H]1CCC(=O)N1C12CC3CC(CC(C3)C1)C2
N-[Adamantan-1-yl]-(L)-Pyroglutamide

Reactants

NC12CC3CC(CC(C3)C1)C2
adamantanamine
O=C1CC[C@@H](C(=O)O)N1
(L)-pyroglutamic acid
CCN(CC)CC
triethylamine
CC(C)(C)C(=O)Cl
pivaloyl chloride

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherslowly at -5°

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04661512uspto-grants-1987_04