Sodium Methoxide → HCID 58928994, compound

HRID 853641Notes

Reaction equation

HRID 853641 reaction equation
C([O:4][C:5]([C:7]1[C:12]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17](=[O:29])[CH2:16]2)=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1)=O)(C)C.C[O-].[Na+]>CO>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:18]2[C:17](=[O:29])[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][CH2:19]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58928880HCID 58928880, compound

Product 1

HCID 58928994HCID 58928994, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 36 (0.900 g, 2.26 mmol) in 12 mL of dry MeOH under a N2 atmosphere was added 12.5 mL of a 0.5 M sodium methoxide (NaOMe). The solution was stirred at ambient temperature for 2.5 hours. The reaction was worked up by removing the solvent and dissolving the residue in CH2Cl2. The organic layer was washed with a saturated aqueous solution of NH4Cl and dried to provide 610 mg of the product 37 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 3.58 (t, 2H, J=6 Hz), 4.308 (t, 2H, J=5 Hz), 4.77 (s, 2H), 7.09 (t, 2H, J=8 Hz), 7.34 (t, 2H, J=8 Hz), 7.61 (dd, 1H, J=5.8 Hz), 8.73 (d, 1H, J=8 Hz), 9.12 (d, 1H, J=3 Hz), 13.00 (s, 1H); 13C NMR (75 M, CDCl3) δ 38.8, 43.9, 49.5, 111.9, 115.9, 116.2, 124.7, 130.0, 130.1, 131.0, 136.4, 146.8, 147.2, 154.7, 157.3, 163.0 (d, J=245 Hz), 163.7; 19F NMR (282.6 MHz, CDCl3) δ 63.2; EI MS (m/z) 340.5 [MH+], 362.3 [M+Na].

Workup

  1. customby removing the solvent
  2. dissolutiondissolving the residue in CH2Cl2
  3. washThe organic layer was washed with a saturated aqueous solution of NH4Cl
  4. customdried

Sources & evidence

ORD record
ord-499210ab0cc1464d8aab1ce8ae683c6e
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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