Sodium Methoxide → HCID 67070097, compound

HRID 2390855Notes

Reaction equation

HRID 2390855 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:6]=[CH:7][C:8]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[C:15]([C:17]2[C:18](=[O:24])[NH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[CH:14]=[C:13]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]=1[O:29][CH3:30].[CH3:36][O-:37].[Na+]>CO>[C:25]([C:13]1[C:12]([O:29][CH3:30])=[C:11](/[CH:10]=[CH:9]/[C:8]2[CH:7]=[CH:6][C:5]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:4][C:3]=2[CH2:2][O:37][CH3:36])[CH:16]=[C:15]([C:17]2[C:18](=[O:24])[NH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[CH:14]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67286846HCID 67286846, compound

Product 1

HCID 67070097HCID 67070097, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

step 3—To a solution of 320 (70 mg, 0.125 mmol) in MeOH (10 mL) was added sodium methoxide (10 mL, 5 mmol, 0.5 M MeOH solution). The reaction was stirred at RT overnight. The reaction mixture was concentrated, diluted with EtOAc and acidified with 6N HCl (1 mL). The organic extract was dried (Na2SO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC plate developed with 2:1 EtOAc/hexane to afford 28 mg of I-208 as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on a preparative SiO2 TLC plate
  8. customto afford 28 mg of I-208 as an off-white solid

Sources & evidence

ORD record
ord-917cace5fc394cad9c07c05c5e81a23b
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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