4-Methylmorpholine → 4-{2-[2-(S)-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-acetyl}-benzoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid	HCID 7009590	—
Reactant	Methyl 4-(2-aminoacetyl)benzoate hydrochloride	HCID 67046619	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-{2-[2-(S)-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-acetyl}-benzoic acid methyl ester	HCID 67046992	73.8%

Reaction Steps

4-(2-Amino-acetyl)-benzoic acid methyl ester hydrochloride (2.22 mmol), WSC.HCl (2.44 mmol), Boc-N-methyl-(L)-alanine (2.44 mmol) and HOBt (2.77 mmol) were suspended in dichloromethane (10 ml). NMM (2.44 mmol) was added and the reaction stirred for 2 h. The reaction was diluted with ethyl acetate (50 ml) and washed with 10% citric acid (2×25 ml) and saturated sodium hydrogen carbonate (2×25 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give a brown oil residue. Purification by silica chromatography eluting with 10-50% ethyl acetate/iso-hexane gave the title compound (620 mg) as a pale yellow oil m/z=379 in MS ES+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915300B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-3fc96cd0b2cc41f7b408ba279598aaca
Source note	uspto-grants-2011_03