Isopropylamine → 1-Benzyl 4-tert-butyl 2-[(isopropylamino)carbonyl]piperazine-1,4-dicarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Isopropylamine	HCID 6363	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	N-4-Boc-N-1-Cbz-2-piperazine carboxylic acid	HCID 2756777	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-Benzyl 4-tert-butyl 2-[(isopropylamino)carbonyl]piperazine-1,4-dicarboxylate	HCID 21059984	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

1-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid 47-1 (0.40 g, 1.10 mmol), 1-hydroxybenzotriazole (0.20 g, 1.32 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.27 g, 1.43 mmol), 4-methylmorpholine (0.0.44 g, 4.39 mmol) and isopropyl amine (0.071 g, 1.21 mmol) were dissolved in DMF and stirred at 25° C. for 18 hours. The DMF was then removed under reduced pressure and the residue partitioned between ethyl acetate and dilute aqueous KHSO4. The aqueous phase was drawn off and the organic layer was washed with dilute aqueous NaHCO3, brine, dried, filtered and evaporated to afford 47-2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115597B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-8ee0ded6dd8e49ac8d719aeddf23bf90
Source note	uspto-grants-2006_10