Methanol → HCID 9954983, compound

HRID 272285Notes

Reaction equation

HRID 272285 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([NH:29]C(OC)=O)([CH3:28])[CH2:26][OH:27])=[C:18]([Cl:34])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O1CCCC1.CO>O>[NH2:29][C:25]([CH3:28])([CH2:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)=[CH:17][C:18]=1[Cl:34])[CH2:26][OH:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 59837341HCID 59837341, compound

Product 1

HCID 9954983HCID 9954983, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound of Example 206 (527 mg) was dissolved in a mixed solvent composed of a 5 mol/L aqueous solution of potassium hydroxide (2 mL), tetrahydrofuran (2 mL) and methanol (3 mL). This mixture was refluxed and stirred for 4 days. Subsequently, the reaction mixture was diluted with water and was extracted with ethyl acetate. The ethyl acetate layer was then washed with a saturated aqueous solution of sodium chloride, was dried over anhydrous magnesium sulfate, and was then concentrated. The resulting residue was purified on a silica gel column chromatography (aminated silica gel, ethyl acetate:ethanol=20:1) to give the desired product as a pale yellow oil (311 mg).

Workup

  1. temperatureThis mixture was refluxed
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with a saturated aqueous solution of sodium chloride
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationwas then concentrated
  6. customThe resulting residue was purified on a silica gel column chromatography (aminated silica gel, ethyl acetate:ethanol=20:1)

Sources & evidence

ORD record
ord-e2691edc56e24a1c896f75f339a26fc2
Source dataset
uspto-grants-2008_11
Patent number
US07456157B2

Reaction notes

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