Diisopropylethylamine → HCID 86726186, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid	HCID 2734668	—
Reactant	3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one	HCID 4293995	—
Reactant	methyl (1S)-1-[({(1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-[4-(2-pyridinyl)benzyl]pentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate	HCID 16037867	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 86726186	HCID 86726186	83%

Reaction Conditions

Temperature	25 °C

Reaction Steps

A solution containing the product from Example 2C (0.050 g, 0.094 mmol) in THF (0.5 mL) was treated with Boc-L-tert-leucine (0.022 g, 0.096 mmol), DEPBT (0.042 g, 0.140 mmol), and N,N-diisopropylethylamine (0.08 mL, 0.459 mmol), stirred at 25° C. for 2 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. The residue was chromatographed on silica gel eluting with a gradient starting with 50-100% ethyl acetate/chloroform to give the title compound (0.058 g, 83% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07834043B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-429a79e75b554169a3008cb2e54a3f54
Source note	uspto-grants-2010_11