Diisopropylethylamine → 2-[4-({[2-[(Tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]ethyl ethyl methylphosphonate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	Tert-butyl 2-{[4-(hydroxymethyl)benzoyl]amino}-4-thien-2-ylphenylcarbamate	HCID 57607813	—
Reactant	4-(2-{[Ethoxy(methyl)phosphoryl]oxy}ethyl)benzoic acid	HCID 57925966	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	2-[4-({[2-[(Tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]ethyl ethyl methylphosphonate	HCID 57925964	—

Reaction Steps

1,1-dimethylethyl [2-({[4-(hydroxymethyl)phenyl]carbonyl}amino)-4-(2-thienyl)phenyl]carbamate (140 mg, 0.50 mmol), BOP (440 mg, 0.99 mmol), 4-(2-{[ethoxy(methyl)phosphoryl]oxy}ethyl)benzoic acid (90 mg, 0.33 mmol), and DIPEA (0.17 mL, 0.99 mmol) were stirred in DMF (1.1 mL) at 60° C. for 72 hours. The mixture was then diluted with saturated NaHCO3 solution and extracted with EtOAc. The organic layers were then washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification of the crude reaction mixture by MPLC (0-10% MeOH/DCM) resulted in the title compound as a yellow foam. MS cal'd 445 (MH+-Boc), exp 445 (MH+-Boc).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07981874B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-8087cdb1fc6e43bea7b6e8bba7d9b57a
Source note	uspto-grants-2011_07