2,6-Lutidine → tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate

Participants

Role	Name	HCID	Charge
Reactant	2,6-Lutidine	HCID 7937	—
Reactant	(R)-(((Phenylmethoxy)carbonyl)amino)phenylacetic acid	HCID 87183	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	(S)-tert-Butyl 2-amino-3-(tert-butoxy)propanoate	HCID 6993439	—
Solvent	Dichloromethane	HCID 6344	—
Product	tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate	HCID 69551729	97.3%

Reaction Conditions

Temperature	0 °C

Reaction Steps

(2R)-{[(Benzyloxy)carbonyl]amino}(phenyl)acetic acid (Z-(R)-Phg-OH) (2.0 g, 7.0 mmol) and tert-butyl O-(tert-butyl)-L-serinate (2.0 g, 7.9 mmol) and 2.6-lutidine were dissolved in DCM (30 ml). After stirring 5 minutes at 0° C. TBTU (2.5 g, 7.8 mmol) was added and stirring was continued 30 minutes at 0° C. and 4 hours at room temperature. The reaction mixture was washed with water (2×100 ml), dried and purified with flash chromatography (DCM) to give the title compound (3.3 g, 97%). NMR (300 MHz, CD3OD): 1.05 (s, 9H), 1.45 (s, 9H), 3.4-3.8 (m, 2H), 4.5 (bs, 1H), 4.85 (s, 2H), 5.1 (s, 2H), 5.4 (s, 1H), 7.25-7.5 (m, 10 H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07470678B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-908f2687bda34762a2f8bdb1636f3e92
Source note	uspto-grants-2008_12