Cornforth reagent → HCID 59722681, compound

HRID 1664862Notes

Reaction equation

HRID 1664862 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C@H:30]1[CH2:36][NH:35]/[C:34](=[N:37]\[CH2:38][CH:39](O)[CH2:40][C:41]([F:44])([F:43])[F:42])/[C@H:33]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:32][CH2:31]1>C(#N)C>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C@H:30]1[CH2:36][N:35]2[C:39]([CH2:40][C:41]([F:44])([F:43])[F:42])=[CH:38][N:37]=[C:34]2[C@H:33]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 178453873HCID 178453873, compound

Product 1

HCID 59722681HCID 59722681, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridinium dichromate (2.24 g, 5.94 mmol) was added to a solution of tert-butyl {(2Z,3R,6S)-6-(2,6-difluorophenyl)-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]azepan-3-yl}carbamate (461 mg, 0.99 mmol) in acetonitrile (20 mL). After 18 h, the mixture was filtered and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (80% hexanes/ethyl acetate→50% hexanes/ethyl acetate) gave the title compound. MS 446.2 (M+1).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. additionSaturated aqueous sodium bicarbonate was added
  4. extractionthe mixture was extracted with dichloromethane (3×)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (80% hexanes/ethyl acetate→50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7f51d14bea354712b3153d19d20d4f85
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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