Water → HCID 22672092, compound

HRID 1006561Notes

Reaction equation

HRID 1006561 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=2[O:19][CH3:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][Li].O>C1COCC1.C(OCC)C>[C:1]1([S:7]([NH:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]([OH:16])[CH3:21])=[CH:13][C:12]=2[O:19][CH3:20])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22672036HCID 22672036, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22672092HCID 22672092, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-phenylsulfonylamino-3-methoxybenzaldehyde (400 mg; prepared in Reference Example 44.) in THF (10 ml) was cooled to at −78° C. mg; prepared in Reference Example 44.) in THF (10 ml) was cooled to at −78° C. in a stream of argon. A solution of methyl lithium (1.0M) in diethyl ether (3.4 ml) was added dropwise thereto. The mixture was stirred for 20 minutes. After the termination of reaction, a mixture of H2O+1N HCl was added thereto to stop the reaction. The mixture was extracted with ethyl acetate three times. The organic layer was washed, dried over and purified on silica gel column chromatography (AcOEt:hexane=1:1) to give the title compound (421 mg) having the following physical data.

Workup

  1. customprepared in Reference Example 44
  2. customAfter the termination of reaction
  3. additionwas added
  4. customthe reaction
  5. extractionThe mixture was extracted with ethyl acetate three times
  6. washThe organic layer was washed
  7. customdried over and
  8. custompurified on silica gel column chromatography (AcOEt:hexane=1:1)

Sources & evidence

ORD record
ord-a3c92d60abf3487d9310bb566fdea860
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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