Diisopropylethylamine → Benzyl[(1S)-2-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N-(Benzyloxycarbonyl)-L-serine	HCID 100310	—
Reactant	N-BOC-ethylenediamine	HCID 187201	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Benzyl[(1S)-2-({2-[(tert-butoxycarbonyl)amino]ethyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate	HCID 131727162	—

Reaction Steps

1.05 g (2.759 mmol) of HATU and 648.3 mg (5.016 mmol) of N,N-diisopropylethylamine are added to a solution of 600 mg (2.5 mmol) of N-[(benzyloxy)carbonyl]-L-serine in 25 ml of anhydrous DMF. After stirring at RT for 15 min, 442.0 mg (2.76 mmol) of tert-butyl(2-aminoethyl)carbamate are added. The reaction mixture is stirred at RT for 15 h. The solvent is then evaporated and the residue is taken up in dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The crude product is purified by preparative HPLC.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07446102B2
Source dataset	uspto-grants-2008_11
ORD ID	ord-7324fe4098a248fe8c32cd8e15095782
Source note	uspto-grants-2008_11