Diisopropylethylamine → methyl (1S,2S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2-methylbutylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one	HCID 4293995	—
Reactant	5-tert-Butyloxycarbonylamino-2-amino-3-hydroxy-1,6-diphenylhexane, (2S,3S,5S)-	HCID 11997926	—
Reactant	L-Isoleucine, N-(methoxycarbonyl)-	HCID 28378062	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	methyl (1S,2S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2-methylbutylcarbamate	HCID 86726174	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

A solution of the product from Example 6A (0.50 g, 1.30 mmol) in THF (13 mL) was treated with the product from Example 5A (0.30 g, 1.59 mmol), DEPBT (0.45 g, 1.50 mmol), and N,N-diisopropylethylamine (1.1 mL, 6.31 mmol), stirred at 25° C. for 16 hours, and partitioned between ethyl acetate and 10% Na2CO3 solution. The organic phase was washed with additional 10% Na2CO3 solution and brine, dried over MgSO4, filtered and concentrated to give the title compound, used without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07834043B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-4a4e04c4fbcb4097b89a252dcbc228bc
Source note	uspto-grants-2010_11