Triethylamine → Z-Asp(OtBu)-Val-OtBu

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	L-Aspartic acid, N-((phenylmethoxy)carbonyl)-, 4-(1,1-dimethylethyl) 1-(2,5-dioxo-1-pyrrolidinyl) ester	HCID 11026196	—
Reactant	tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride	HCID 12490702	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Z-Asp(OtBu)-Val-OtBu	HCID 70050186	81.7%

Reaction Steps

1.68 ml (12.0 mmol) of triethylamine are added to a suspension containing 2.58 g (12.0 mmol) of H-Val-OtBu.HCl and 4.62 g (11.0 mmol) of Z-Asp(OtBu)-OSu in 25 ml of dimethylformamide (DMF). The reaction mixture is left to stand overnight, then evaporated under reduced pressure. The residue is mixed with 50 ml of ethyl acetate and the suspension obtained is successively washed with 25 ml of water, 3 times with 25 ml of 1 mol/liter hydrochloric acid each, 3 times with 25 ml of 5% aqueous sodium hydrogenocarbonate each and finally with 25 ml of water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain 4.3 g (81.7%) of oily Z-Asp(OtBu)-Val-OtBu protected dipeptide, Rf1 =0.85.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05093320
Source dataset	uspto-grants-1992_03
ORD ID	ord-80e1ff23442740fab22af43a8ce136fb
Source note	uspto-grants-1992_03