Ammonium Hydroxide → 2-((Diethoxvphosphoryl)methylamino)-2-(furan-2-yl)acetic acid

HRID 28760Notes

Reaction equation

HRID 28760 reaction equation
[NH2:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.O.[C:20]([OH:24])(=[O:23])[CH:21]=O.[NH4+].[OH-]>ClCCl.C(OCC)(=O)C.CO.C(#N)C>[CH2:5]([O:4][P:3]([CH2:2][NH:1][CH:21]([C:12]1[O:11][CH:15]=[CH:14][CH:13]=1)[C:20]([OH:24])=[O:23])([O:7][CH2:8][CH3:9])=[O:10])[CH3:6]

Participants

9

Reactant 4

HCID 14923Ammonium HydroxideHCID 1596920Diethyl (aminomethyl)phosphonateHCID 2734357Furan-2-boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 114150762-((Diethoxvphosphoryl)methylamino)-2-(furan-2-yl)acetic acidYield 67%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl aminomethylphosphonate, prepared according to literature (Davidsen, S. K.; Philips, G. W.; Martin, S. F. Organic Synthesis CV 8, 451.) (50 mg, 0.3 mmol), 2-furan boronic acid (67 mg, 0.6 mmol), glyoxylic acid monohydrate (28 mg, 0.3 mmol) was put into a 10ml round bottom flask, dissolved with 5 ml of acetonitrile. The mixture was stirred at room temperature for one day. Solvent was then removed and product was isolated by flash column chromatography using NH4OH 5%, MeOH 20%, ethyl acetate 55%, dichloromethane 20% afforded 60 mg clear oil (67% yield). 1H NMR (360 MHz, CDCl3) δ 1.23-1.33(td, J=7.3, 1.7 Hz, 6H), 2.86-2.98(d, J=13.3 Hz, 2H), 4.02-4.14(m, 4H), 4.49(s, 1H), 6.26-6.31(dd, J=3.2, 1.8 Hz, 1H), 6.31-6.36(d, J=3.2 Hz, 1H), 7.33-7.38(bs, 1H); 13C NMR (126 MHz, CDCl3) δ 16.30(d, J=6 Hz), 41.51(d, J=156.5 Hz), 60.81(d, J=14.7 Hz), 62.40(t, J=6.8 Hz), 108.97, 110.27, 142.41, 151.19, 173.29.

Workup

  1. customwas put into a 10ml round bottom flask
  2. customSolvent was then removed
  3. customproduct was isolated by flash column chromatography

Sources & evidence

ORD record
ord-28fc6d619c8e414c883565099c670c3c
Source dataset
uspto-grants-2008_09
Patent number
US07420000B2

Reaction notes

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