Benzyl Bromide → HCID 15659558, compound

Participants

Role	Name	HCID	Charge
Reactant	Benzyl Bromide	HCID 7498	—
Reactant	2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-	HCID 81646	—
Reactant	Lithium Hexamethyldisilazide	HCID 2733832	—
Reactant	[(S)-2-(4-Benzyloxy-phenyl)-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester	HCID 54401688	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 15659558	HCID 15659558	—

Reaction Steps

Analogously to Example 21 D) 1)c), 2.47 g (6.0 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-benzyloxyphenyl)ethyl]-dihydrofuran-2-(3H)-one dissolved in 12 ml of THF and 1.2 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone are deprotonated at -70° C. with 11.73 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated (75 min) with 0.713 ml (6.0 mmol) of benzyl bromide in 3 ml of THF. Column chromatography (SiO2, hexane/ethyl acetate 4:1→2:1) and crystallisation from ether/hexane yields the pure title compound: TLC Rf (D)=0.36.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05643878
Source dataset	uspto-grants-1997_07
ORD ID	ord-ffd33054348d4e809cb5974f64002fe9
Source note	uspto-grants-1997_07