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Cesium carbonate → Tert-butyl (4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate

HRID 1184134
Notes
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Reaction equation

HRID 1184134 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:17]([O-:19])=[O:18])=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.CS(O[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][N:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[N+:17]([O-:19])=[O:18])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10587951Tert-butyl (3-methoxy-2-nitrophenyl)carbamateHCID 116870064-Methoxybutyl methanesulfonate

Product 1

HCID 58355557Tert-butyl (4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamateYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
65 °C

Procedure

tert-Butyl (3-methoxy-2-nitrophenyl)carbamate (3.00 g) and 4-methoxybutyl methanesulfonate (3.06 g) were dissolved in dimethylformamide (40 ml), cesium carbonate (7.30 g) was added, and the mixture was stirred at 65° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over s anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-7:3) was concentrated under reduced pressure to give the object product (2.11 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over s anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washa fraction eluted with ethyl acetate-hexane (5:95-7:3)
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-8612a31a65714142bdbbdf4a90fe0143
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664380B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes