Water → HCID 178523577, compound

HRID 1263535Notes

Reaction equation

HRID 1263535 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:40])[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[CH2:25][CH2:24]1)(C(C)(C)C)(C)C.ClC(Cl)C.O.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][C:30](=[O:40])[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 63651,1-DichloroethaneHCID 6422Trifluoroacetic acidHCID 178455055HCID 178455055, compound

Product 1

HCID 178523577HCID 178523577, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottomed flask was added trans-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]-3-nitrobenzamide (52 mg), dichloroethane (9 ml), water (3 ml), and trifluoroacetic acid (3 ml). The reaction mixture was heated under reflux for 15 hr, cooled to room temperature, and toluene (15 ml) was added. The reaction mixture was concentrated in vacuo, methanol (15 ml) was added, and further concentrated to remove residual trifluoroacetic acid. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:3, then 1:1, v/v) furnished the title compound (20 mg, 63%) as a white solid. δH ((CD3)2CO): 1.52-1.68 (4H, m), 1.87-1.95 (2H, m), 2.09-2.17 (2H, m), 2.87 (1 H, tt), 3.97-4.08 (1 H, m), 6.30 (1 H, dd), 6.38 (1 H, d), 6.99 (1 H, d), 7.77 (1H, t), 7.90 (1H, s), 7.96 (1 H, d), 8.05 (1 H, s), 8.33 (1 H, dd), 8.37 (1 H, dd), 8.68 (1 H, t); m/z (ES+) 357 )M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 15 hr
  3. concentrationThe reaction mixture was concentrated in vacuo, methanol (15 ml)
  4. additionwas added
  5. concentrationfurther concentrated
  6. customto remove residual trifluoroacetic acid
  7. customPurification via flash chromatography (
  8. washSiO2, ethyl acetate/petroleum ether, gradient elution

Sources & evidence

ORD record
ord-de53f0d5b9b449db86e8180d2afd9d50
Source dataset
uspto-grants-2003_04
Patent number
US06541473B2

Reaction notes

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