Diisopropylethylamine → tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733286	—
Reactant	(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate	HCID 10803731	—
Reactant	4-(3-Methoxy-3-oxopropyl)benzoic acid	HCID 11310294	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate	HCID 15512203	—

Reaction Steps

354 mg (1.7 mmol) of 4-(2-methoxycarbonylethyl)benzoic acid (Example 3b) and 500 mg (1.7 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-amino-propionate were dissolved in 3 ml of DMF and treated with 557 mg (1.7 mmol) of O-[[(cyano(ethoxycarbonyl)methylidene)amino]-1,1,3,3,-tetramethyluronium tetrafluoroborate (TOTU) and 204 mg (1.7 mmol) of diisopropylethylamine (DIPEA) and the solution was stirred at RT for 7 h. The solvent was evaporated in vacuo, the residue was dissolved in ethyl acetate (EA) and washed three times each with KHSO4 and NaHCO3 solution until neutral, the organic phase was separated off and dried, and the solvent was distilled off in vacuo. Yield: 770 mg (93%). MS: ES+, m/e=485.2 (M+H+, 100%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07348333B2
Source dataset	uspto-grants-2008_03
ORD ID	ord-1b28375b2e554929b0f572a61354a398
Source note	uspto-grants-2008_03