Cesium carbonate → HCID 59496631, compound

HRID 449515Notes

Reaction equation

HRID 449515 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].F[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[C:9]([O:8][C:7]([NH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:16]=[CH:15][CH:14]=1)[O:1][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=[O:13])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67878Methyl 4-fluorobenzoateHCID 18369568tert-butyl N-((3-hydroxyphenyl)methyl)carbamate

Product 1

HCID 59496631HCID 59496631, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl (3-hydroxybenzyl)carbamate (0.025 g, 0.11 mmol) was dissolved in acetonitrile (1.0 mL) with methyl 4-fluorobenzoate (Aldrich, Cat 120707) (0.034 g, 0.22 mmol) and cesium carbonate (0.073 g, 0.22 mmol) in a sealed tube. The reaction was heated to 100° C. for 2 h. and was complete. The reaction was taken up in ethyl acetate, filtered and concentrated under reduced pressure to give crude methyl 4-(3-((tert-butoxycarbonylamino)methyl)phenoxy)benzoate (0.040 g) as a clear oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9ebf6160880433391f45dcdf6cb63a5
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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