Benzyloxycarbonyl-L-phenylalanine → HCID 22876169, compound

Participants

Role	Name	HCID	Charge
Reactant	Benzyloxycarbonyl-L-phenylalanine	HCID 70878	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733286	—
Reactant	Ethyl 2-cyano-2-(hydroxyimino)acetate	HCID 6399078	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 22876169	HCID 22876169	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

31.8 ml (0.18 mol) of N-ethyldiisopropylamine are added dropwise, at 0° C., to a solution of 17.94 g (0.06 mol) of benzyloxycarbonylphenylalanine, 5.97 g (0.06 mol) of N,O-dimethylhydroxylamine hydrochloride, 8.79 g (0.06 mol) of ethyl hydroxyiminocyanoacetate and 19.68 g (0.06 mol) of TOTU in 120 ml of DMF. The mixture is stirred at 0° C. for 1 h and at RT for 3 h. The solvent is removed by rotary evaporation i.V. and the residue is taken up in ethyl acetate; the solution thus obtained is washed several times with a 10% solution of citric acid, with a 10% solution of KHCO3 and with a saturated solution of NaCl. Once the solution has been dried over Na2SO4 and filtered, and the filtrate has been concentrated, 13.95 g (68%) of an oil remain.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05663139
Source dataset	uspto-grants-1997_09
ORD ID	ord-9248da4855484db2aebaa4431fc3727d
Source note	uspto-grants-1997_09