Methanol → HCID 15337848, compound

HRID 1993115Notes

Reaction equation

HRID 1993115 reaction equation
[C:1]([O:5][C:6]([N:8](C1C=CN=CC=1)[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH:22]1(N=C=NC2CCCCC2)CCCCC1.[N:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(OCC)(=O)C>[CH3:4][C:1]([CH3:2])([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:40]1[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=1)[C:11]([O:13][CH3:22])=[O:12])=[O:7])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 23381534HCID 23381534, compound

Product 1

HCID 15337848HCID 15337848, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a flask was charged with phosphonic acid 1 (67 mg, 0.1 mmol), methanol (0.1 mL, 2.5 mmol) and 1,3-dicyclohexylcarbodiimide (83 mg, 0.4 mmol), then pyridine (1 mL) was added under N2. The resulted mixture was stirred at 60-70° C. for 2 h, then cooled to room temperature and diluted with ethyl acetate. The mixture was filtered and the filtrate was evaporated. The residue was diluted with ethyl acetate and the combined organic phase was washed with NH4Cl, brine and water, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel (isopropanol/CH2Cl2, 1% to 7%) to give 2 (39 mg, 56%) as a white solid. 1H NMR (CDCl3) δ 7.71 (d, J=8.7 Hz, 2H), 7.15 (d, J=8.7 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 5.65 (d, J=5.1 Hz, 1H), 5.10-4.92 (m, 4H), 4.26 (d, J=9.9 Hz, 2H), 3.96-3.65 (m overlapping s, 15H), 3.14-2.76 (r, 7H), 1.81-1.55 (m, 3H), 0.91 (d, J=6.6 Hz, 3H), 0.88 (d, J=6.6 Hz, 3H); 31P NMR (CDCl3) δ 21.7; MS (ESI) 723 (M+Na).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was diluted with ethyl acetate
  5. washthe combined organic phase was washed with NH4Cl, brine and water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (isopropanol/CH2Cl2, 1% to 7%)

Sources & evidence

ORD record
ord-91da950540dd4d6db9461797110ffeae
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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