tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate → HCID 86620122, compound

HRID 1664821Notes

Reaction equation

HRID 1664821 reaction equation
F[C:2]1[C:7](F)=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][NH:14][C:13](=[O:16])[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1.[H][H]>C(O)(=O)C.[Pt]=O>[CH:3]1([C@H:9]2[CH2:15][NH:14][C:13](=[O:16])[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:11][CH2:10]2)[CH2:2][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 23657400tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86620122HCID 86620122, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Platinum oxide (300 mg, 1.32 mmol) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-ylcarbamate (463 mg, 1.36 mmol) in glacial acetic acid (15 mL) and the mixture hydrogenated under 50 psi hydrogen in a Parr apparatus. After 3 d, the mixture was concentrated. Saturated aqueous sodium bicarbonate was added, and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (hexanes→55% ethyl acetate/hexanes) gave the title compound (210 mg). MS 311.2 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (hexanes→55% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-874c7739294349259de6cc63f8bebc9b
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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