Diisopropylethylamine → HCID 86726230, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	—
Reactant	HCID 42626250	HCID 42626250	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 86726230	HCID 86726230	56.3%

Reaction Conditions

Temperature	25 °C

Reaction Steps

A solution containing the product from Example 2C (0.074 g, 0.138 mmol) in THF (1.5 mL) was treated with the product from Example 124A (0.051 g, 0.152 mmol), DEPBT (0.062 g, 0.207 mmol), and N,N-diisopropylethylamine (0.120 mL, 0.691 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. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane, followed by 0-5% methanol in ethyl acetate to give the title compound (0.066 g, 56% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07834043B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-5c0ea796fb70460b80d39a15a569552a
Source note	uspto-grants-2010_11