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

HRID 270088Notes

Reaction equation

HRID 270088 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>[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

5

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%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-(acetylamino)-3-hydroxyphenyl acetate (669 mg, 3.2 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (748 mg, 2.9 mol) and caesium carbonate (1.05 g, 3.2 mmol) in 1-methyl-pyrrolidinone (10 mL) was stirred over night at room temperature, and then partitioned between water and ethyl acetate. The organic phase was washed twice with water and concentrated to an yellow oil, which was suspended in methanol/diethyl ether, ½. The precipitated beige solid was filtered off and dried to give the titled compound (296 mg, 38%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic phase was washed twice with water
  3. concentrationconcentrated to an yellow oil, which
  4. filtrationThe precipitated beige solid was filtered off
  5. customdried

Sources & evidence

ORD record
ord-ef6711d061bc446fb7709b68a6d153aa
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

Loading…