Cesium carbonate → HCID 86612853, compound

HRID 1782027Notes

Reaction equation

HRID 1782027 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[OH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29]1)=[O:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[O:1]1[CH2:3][C@H:2]1[CH2:4][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([N:28]1[CH2:32][CH2:31][C@H:30]([OH:33])[CH2:29]1)=[O:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 69016786HCID 69016786, compound

Product 1

HCID 86612853HCID 86612853, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (228 mg, 0.88 mmol), (3S)-1-[(2-hydroxyphenyl)acetyl]pyrrolidin-3-ol (196 mg, 0.88 mmol) and Cs2CO3 (344 mg, 1.05 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography/(0-3% methanol in dichloromethane) to give the subtitled compound (35 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography/(0-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c6bbb2234f50476c840d4ff4dd8187cf
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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