Sodium Methoxide → HCID 58928879, compound

HRID 853636Notes

Reaction equation

HRID 853636 reaction equation
C([O:4][C:5]([C:7]1[C:12]([C:13]([N:15]2[CH2:20][C:19](=[O:21])[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:17](=[O:30])[CH2:16]2)=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1)=O)(C)C.C[O-].[Na+]>>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:18]2[C:17](=[O:30])[C:16]3[N:15]([C:13](=[O:14])[C:12]4[CH:11]=[CH:10][CH:9]=[N:8][C:7]=4[C:5]=3[OH:4])[CH2:20][C:19]2=[O:21])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 58928875HCID 58928875, compound

Product 1

HCID 58928879HCID 58928879, compound

Procedure

A solution of 31 (5 mg, 0.01 mmol) in 0.3 mL of dry 0.5 M NaOMe was stirred at ambient temperature for 15 minutes when a yellow precipitate formed. The solvent was removed in vacuo and the solid was dissolved in a mixture of CH2Cl2— 1N HCl. The layers were separated and the aqueous layer was washed with CH2Cl2. The organic solvent was removed to provide an off-white solid. The product 32 was purified by trituration using CH2Cl2 and hexane. 1H NMR (300 MHz, CDCl3) δ 5.01 (s, 2H), 5.16 (s, 2H), 7.02 (dt, 2H, J=2, 9 Hz), 7.51 (ddd, 2H, J=2, 5, 9 Hz), 7.79 (dd, 1H, J=8, 5 Hz), 8.61 (dd, 1H, J=8, 2 Hz), 9.13 (dd, 1H, J=4, 2 Hz), 12.35 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 42.4, 46.1 107.0, 115.5, 115.8, 126.7, 127.1, 130.8, 131.4, 131.5, 132.5, 143.2, 148.4, 153.7, 156.0, 162.2 (d, J=249 Hz), 163.9, 164.0; EI MS (m/z) 354.6 [MH+].

Workup

  1. customformed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe solid was dissolved in a mixture of CH2Cl2— 1N HCl
  4. customThe layers were separated
  5. washthe aqueous layer was washed with CH2Cl2
  6. customThe organic solvent was removed
  7. customto provide an off-white solid
  8. customThe product 32 was purified by trituration

Sources & evidence

ORD record
ord-53e3f4c33ab746d0bb7f9e89105a4d2a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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