Sodium Methoxide → HCID 90411588, compound

HRID 1754614Notes

Reaction equation

HRID 1754614 reaction equation
C[O-].[Na+].[C:4]([Si:8]([CH3:40])([CH3:39])[O:9][CH2:10][C@H:11]([CH2:22][N:23]1[CH:28]=[CH:27][C:26](=[O:29])[N:25](C(=O)C2C=CC=CC=2)[C:24]1=[O:38])[C@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:13])([CH3:7])([CH3:6])[CH3:5].[Cl-].C([NH+](CC)CC)C>CO>[C:4]([Si:8]([CH3:39])([CH3:40])[O:9][CH2:10][C@H:11]([CH2:22][N:23]1[CH:28]=[CH:27][C:26](=[O:29])[NH:25][C:24]1=[O:38])[C@H:12]([O:14][Si:15]([C:18]([CH3:20])([CH3:21])[CH3:19])([CH3:17])[CH3:16])[CH3:13])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12698378Triethylazanium chlorideHCID 90410736HCID 90410736, compound

Product 1

HCID 90411588HCID 90411588, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium methoxide, 25% in MeOH (6 ml) was added to asolution of 41 (8.7 g, 15.9 mmol) in 300 ml of MeOH. The reaction was stirred at 50° C. for 3 hrs, then treated with 5.3 g of solid triethylammonium chloride and concentrated. The obtained residue was partitioned between water and ethyl acetate. The organicphase was washed with saturated NaCl and dried over Na2SO4. Concentration of the extract gave an oil. The oil was chromatographed on silica eluting with 20 to 30% ethyl acetate in hexane to afford a crude product, which was re-crystallized from hexane (˜30 ml) at −20° C. to yield 5.4 g (76%) of 42 as white crystals. 1H NMR (DMSO-d6): δ 11.18 (s, 1H), 7.49 (d, J=7.5 Hz, 1H), 5.51 (d, J=7.5 Hz, 1H), 3.99 (m, 1H), 3.75 (m, 1H), 3.55 (m, 3H), 2.03 (m, 1H), 1.12 (d, J=6 Hz, 3H), 0.84 (s, 18H), 0.02 (s, 6H), 0.00 (s, 6H).

Workup

  1. concentrationconcentrated
  2. customThe obtained residue was partitioned between water and ethyl acetate
  3. washThe organicphase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. customConcentration of the extract gave an oil
  6. customThe oil was chromatographed on silica eluting with 20 to 30% ethyl acetate in hexane
  7. customto afford a crude product, which
  8. customwas re-crystallized from hexane (˜30 ml) at −20° C.

Sources & evidence

ORD record
ord-fc469b2e162c4234b3cfa7a9218463b3
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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