Water → methyl N-benzyl-O-[tert-butyl(dimethyl)silyl]-D-serinate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Triethylamine	HCID 8471	—
Reactant	tert-Butyldimethylsilyl chloride	HCID 28928	—
Reactant	(R)-Methyl 2-(benzylamino)-3-hydroxypropanoate	HCID 11063677	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	methyl N-benzyl-O-[tert-butyl(dimethyl)silyl]-D-serinate	HCID 15456533	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To methyl N-benzyl-D-serinate (1 eq.) in CH2Cl2 (0.3 M) at rt were added triethylamine (1 eq) and DMAP (0.05 eq). The reaction mixture was cooled to 0° C. and TBS-Cl (1.1 eq) was added. The reaction mixture was stirred at rt for 16 hrs, water was added and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with saturated aqueous NH4Cl, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315475B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-c6c050d3adef4c7d97e4d290493d254e
Source note	uspto-grants-2016_04