Cesium carbonate → 4-(acetylamino)-3-[(2S)-oxiran-2-ylmethoxy]phenyl acetate

HRID 2112741Notes

Reaction equation

HRID 2112741 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([OH:15])[CH:6]=1)(=[O:3])[CH3:2].[N+](C1C=C(S(O[CH2:29][C@@H:30]2[CH2:32][O:31]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN1CCCC1=O.CO.C(OCC)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([O:15][CH2:29][C@@H:30]2[CH2:32][O:31]2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 688181524-Acetamido-3-hydroxyphenyl acetate

Product 1

HCID 715703414-(acetylamino)-3-[(2S)-oxiran-2-ylmethoxy]phenyl acetateYield 38.5%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

A mixture of 4-(acetylamino)-3-hydroxyphenyl acetate (669 mg, 3.2 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (748 mg, 2.9 mmol) and Cs2CO3 ((1.05 g, 3.2 mmol) in 1-methyl-pyrrolidinone (10 mL) was stirred at room temperature over night. The reaction mixture was partitioned between ethyl acetatwe and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give a yellow oil which was suspended in methanol/diethyl ether. The precipitate was filtered off and dried to give the sub-title compound (296 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetatwe and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil which
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-34e02ff61af84e5389eb2c50ab9fc451
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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