Diisopropylamine → ethyl (alphaS)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4'-ethoxymethyl-2',6'-dimethoxy(1,1'-biphenyl)-4-propionate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate	HCID 10789275	—
Reactant	2,6-Dimethoxy-4-(ethoxymethyl)phenylboric acid	HCID 23080950	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	ethyl (alphaS)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4'-ethoxymethyl-2',6'-dimethoxy(1,1'-biphenyl)-4-propionate	HCID 11329259	123.2%

Reaction Conditions

Temperature	90 °C

Reaction Steps

Under nitrogen atmosphere, to a mixture of ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(trifluoromethanesulfonyloxy)benzenepropionate (66.2 g), 4-ethoxymethyl-2,6-dimethoxyphenylboric acid (54.0 g), triphenylphosphine (9.83 g) and N-methylpyrrolidone (330 ml) were added palladium acetate (1.68 g) and diisopropylamine (24.9 g), and the mixture was heated at 90° C. After stirring for 1 hour at the same temperature, the mixture was cooled and toluene and water were added. The organic layers were washed with 10% aqueous citric acid solution and saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was removed in vacuo to yield ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate (90.1 g) as oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07476758B2
Source dataset	uspto-grants-2009_01
ORD ID	ord-b1731374eedf48cfbe30d4cba0c11c28
Source note	uspto-grants-2009_01