HCID 58869132, compound → HCID 58869160, compound

HRID 2355204Notes

Reaction equation

HRID 2355204 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][C:18](=[O:20])[C:17]2[C:12](=[CH:13][C:14]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:15][CH:16]=2)[O:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:31][Mg]Cl>C1COCC1>[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][C:18]([OH:20])([CH3:31])[C:17]2[C:12](=[CH:13][C:14]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:15][CH:16]=2)[O:11]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 58869132HCID 58869132, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 58869160HCID 58869160, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (7-benzenesulfonyl-4-oxo-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (216 mg, 0.5 mmol) in THF (25 mL) at 0° C. was added MeMgCl (3.0 M in THF, 0.208 mL). The mixture was allowed to warm at room temperature and was stirred for 6 hours. The reaction was quenched by addition of water and it was concentrated in vacuo. The aqueous residue was extracted with DCM and the organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (DCM/MeOH, 97/3) to give (7-benzenesulfonyl-4-hydroxy-4-methyl-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (214 mg, 96% yield) as yellow crystalline solid.

Workup

  1. customThe reaction was quenched by addition of water and it
  2. concentrationwas concentrated in vacuo
  3. extractionThe aqueous residue was extracted with DCM
  4. dry with materialthe organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography (DCM/MeOH, 97/3)

Sources & evidence

ORD record
ord-f1e55cf9bf784cbdb5080aacd8cbc7c6
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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