1,2-Dimethoxyethane → HCID 11363587, compound

HRID 1096471Notes

Reaction equation

HRID 1096471 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([NH:12][C:13](=[O:35])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:27][N:26]([CH3:28])[C:25]4[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=4[O:23]3)=[C:16]([CH3:33])[C:15]=2[CH3:34])[CH:6]=1.COCCOC.[OH-].[Na+].C(COC)(C)(C)C>CO>[CH3:34][C:15]1[C:16]([CH3:33])=[C:17]([O:20][CH2:21][C@@H:22]2[CH2:27][N:26]([CH3:28])[C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[O:23]2)[CH:18]=[CH:19][C:14]=1[C:13]([NH:12][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:36])=[O:2])[CH:10]=[CH:9][C:8]=1[F:11])=[O:35]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 136871Propane, 1-methoxy-2,2-dimethyl-HCID 86609825HCID 86609825, compound

Product 1

HCID 11363587HCID 11363587, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the compound (240 mg) prepared in Example 12, 1,2-dimethoxyethane (5.0 mL), and methanol (5.0 mL), 1N sodium hydroxide solution (3.0 mL) was added, and the mixture was stirred for 1 hour at room temperature. Methyl tert-butylmethyl ether was added to the reaction mixture, which was extracted by 1N sodium hydroxide solution. The water layer was neutralized by adding 5N hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with water and saturated brine solution, and was dried by anhydrous magnesium sulphate. The compound (208 mg) of the present invention having the following physical data was obtained by allowing the residue obtained by removing the solvent to recrystallize from a mixed solvent of n-hexane, ethyl acetate, and tetrahydrofuran.

Workup

  1. additionwas added
  2. extractionwas extracted by 1N sodium hydroxide solution
  3. additionby adding 5N hydrochloric acid
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine solution
  6. dry with materialwas dried by anhydrous magnesium sulphate
  7. customwas obtained
  8. customobtained
  9. customby removing the solvent
  10. customto recrystallize from a mixed solvent of n-hexane, ethyl acetate, and tetrahydrofuran

Sources & evidence

ORD record
ord-3e0adbf29d124bb6bf466c21f55b5453
Source dataset
uspto-grants-2012_03
Patent number
US08138335B2

Reaction notes

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