Water → {4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

HRID 1051226Notes

Reaction equation

HRID 1051226 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:25])O)=[C:10]([N+:26]([O-:28])=[O:27])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:25])=[C:10]([N+:26]([O-:28])=[O:27])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 90103009{4-[2-(2-Chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 90102327{4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of {4-[2-(2-chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (0.45 g, 1.06 mmol)in THF (10 mL) was added 2,2,2-trifluoroacetic anhydride (671 mg, 3.18 mmol) at 25° C. resulting in a color change to dark blue. The reaction was allowed to stir at 25° C. for 30 min after which 8-diazabicyclo[5.4.0]undec-7-ene (0.76 g, 5.00 mmol) was added. The reaction was heated to 70° C. for 3 h and then cooled to 25° C. and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (90/10 hexanes/ethyl acetate) afforded {4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (240 mg, 60%) as an oil.

Workup

  1. customresulting in a color change to dark blue
  2. additionwas added
  3. temperaturecooled to 25° C.
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration
  8. concentrationfollowed by concentration in vacuo
  9. customgave a brown solid

Sources & evidence

ORD record
ord-915310cc52254c31a41c60e1eb95dbdb
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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