Diisopropylethylamine → HCID 86726229, 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 42626249	HCID 42626249	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 86726229	HCID 86726229	61.1%

Reaction Conditions

Temperature	25 °C

Reaction Steps

A solution containing the product from Example 2C (0.082 g, 0.154 mmol) in THF (1.5 mL) was treated with the product from Example 123A (0.057 g, 0.17 mmol), DEPBT (0.069 g, 0.231 mmol), and N,N-diisopropylethylamine (0.135 mL, 0.77 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% acetate/dichloromethane, followed by 0-5% methanol in ethyl acetate to give the title compound (0.080 g, 61% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07834043B2
Source dataset	uspto-grants-2010_11
ORD ID	ord-c21bb9a64d8f4bf7a8783cccf096dc6c
Source note	uspto-grants-2010_11