Triethylamine → HCID 178472285, compound

HRID 1677618Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](N)[CH:16]=1)[CH2:6][P:7]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].OS(C(F)(F)F)(=O)=O.[C:31]([O:35][C:36]([NH:38][C:39]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[NH:40])=[O:37])([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:40][C:39]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[N:38][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[CH2:6][P:7]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

2-(3-aminophenyl)-3-di(ethoxy)phosphinoylpropanoic acid ethyl ester (350.0 mg, 0.96 mmol), N,N′-di(t-butoxycarbonyl)guanidine triflate (375 mg, 0.96 mmol), chloroform (10 mL) and triethylamine (133.4 mL, 0.96 mmol) were combined in a 25 ml flask and stirred at 50° C. for 27 hours. The solvents were evaporated. The resulting residue was dissolved in acetonitrile/water (8 mL) and purified by preparative chromatography. The fractions were combined and evaporated to an oil, which was dried under high vacuum for 48 hours to give 107 mg of 2-(3-N,N′-di(t-butoxycarbonyl)-guanidinophenyl)-3-di(ethoxy)phosphinoylpropanoic acid ethyl ester, which was used in the next step.

Workup

customThe solvents were evaporated
dissolutionThe resulting residue was dissolved in acetonitrile/water (8 mL)
custompurified by preparative chromatography
customevaporated to an oil, which
customwas dried under high vacuum for 48 hours

Sources & evidence

ORD record: ord-e207a36b75784d3fa70923ce09cf945d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008325B2

Reaction notes

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