Methanol → HCID 178470992, compound

HRID 2223237Notes

Reaction equation

C[Si]([O:5][PH:6][O:7][Si](C)(C)C)(C)C.[PH2]([O-])=O.[NH4+].[C:16]([O:20][C:21]([NH:23][C:24]1[N:29]=[CH:28][C:27]([CH2:30][C:31](=[CH2:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].CO>C(Cl)Cl.O>[C:16]([O:20][C:21]([NH:23][C:24]1[N:29]=[CH:28][C:27]([CH2:30][CH:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:37][PH:6](=[O:7])[OH:5])=[CH:26][CH:25]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Bis(trimethylsilyl)phosphonite was generated as described in WO 01/042252 using N,O-bis-(trimethylsilyl)acetamide (3.0 mL; 12.1 mmol) and ammonium hypophosphite (1.0 g; 12.0 mmol). The resulting reaction mixture was cooled to 0° C. and a solution of ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylate (0.72 g; 2.35 mmol), in methylene chloride (4 mL) was added dropwise. The reaction was stirred overnight at room temperature. Methanol was added at 0° C. followed by water. The reaction mixture was concentrated. The remaining residue was dissolved in water and purified by preparative HPLC (0.1 M NH4Ac (aq)/CH3CN, 1/0→0/1), concentrated and lyophilized to afford 0.56 g (64%) of 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropylphosphinic acid.

Workup

customThe resulting reaction mixture
concentrationThe reaction mixture was concentrated
dissolutionThe remaining residue was dissolved in water
custompurified by preparative HPLC (0.1 M NH4Ac (aq)/CH3CN, 1/0→0/1)
concentrationconcentrated

Sources & evidence

ORD record: ord-7ec769bf8de94f5694e26620634af22e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375121B2

Reaction notes

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