Diisopropyl Ether → N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane

Participants

Role	Name	HCID	Charge
Reactant	Diisopropyl Ether	HCID 7914	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanesulfonyl chloride	HCID 31297	—
Reactant	(2R,3S)-3-(t-butoxycarbonyl)amino-4-phenyl-butane-1,2-diol	HCID 11076870	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Heptane	HCID 8900	—
Product	N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane	HCID 10904464	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of the crude N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-butanol obtained in Reference Example 3 and dissolved in ethyl acetate 250 kg were added isopropylether 230 kg, methane sulfonylchloride 34.7 kg at 20-30° C., and triethylamine 30.6 kg and stirring at 30-40° C. for 1 hr. N-heptane was added to the reaction solution and the obtained solution was cooled down to 50° C. or lower to deposit crystals, which were filtered by centrifugation to obtain a wet crystal of crude N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane 153.6 kg (Net.60.6 kg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06376685B1
Source dataset	uspto-grants-2002_04
ORD ID	ord-021fec549efc4c5593f950b0db03fb9d
Source note	uspto-grants-2002_04