Diisopropylethylamine → HCID 69883297, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	(R)-Methyl 2-(methylamino)propanoate hydrochloride	HCID 60149789	—
Reactant	HCID 69950176	HCID 69950176	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 69883297	HCID 69883297	49%

Reaction Steps

To a solution of (R/S)-α-t-butoxycarbonylmethyl-4-benzyloxyphenylacetic acid 48b (4.8 g, 13.48 mmol) and methyl N-methyl-D-alaninate hydrochloride (2.9 g, 18.9 mmol) in DMF (30 mL) cooled in an ice bath was added BOP (6.56 g, 14.83 mmol) followed by DIEA (16.5 mL, 94.5 mmol) and the solution was stirred overnight. EtOAc was added and the solution was washed with NaHCO3 and brine, dried over MgSO4, and concentrated. The residue was purified on a silica gel column by eluting with 40% EtOAc/hexane to give the desired product (3.0 g, 49%) as a solid. MS (CI—NH3): (M+H)+=456.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06376665B1
Source dataset	uspto-grants-2002_04
ORD ID	ord-ebe1d8d9d8794fe3ac5c2fee7ffd080e
Source note	uspto-grants-2002_04