Acetic Anhydride → HCID 86620142, compound

HRID 1664921Notes

Reaction equation

HRID 1664921 reaction equation
C(N(CC)CC)C.[C:8]([CH:10]1[C@H:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][CH2:14][C@@H:13]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=2[F:32])[CH2:12][NH:11]1)#[N:9].[C:33](OC(=O)C)(=[O:35])[CH3:34].C(=O)(O)[O-].[Na+]>ClCCl>[C:33]([N:11]1[CH2:12][C@H:13]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=2[F:32])[CH2:14][CH2:15][C@@H:16]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]1[C:8]#[N:9])(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86620141HCID 86620141, compound

Product 1

HCID 86620142HCID 86620142, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.29 mL, 9.25 mmol) was added to a solution of tert-butyl [(3R,6S)-2-cyano-6-(2,3-difluorophenyl)azepan-3-yl]carbamate (0.65 g, 1.85 mmol) in dichloromethane (20 mL) at 0° C. Acetic anhydride (0.53 mL, 5.55 mmol) was added and the mixture was allowed to warm to ambient temperature. After 16 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (99% dichloromethane/ethyl acetate→70% dichloromethane/ethyl acetate) gave the title compound (144 mg). MS 394.1 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (99% dichloromethane/ethyl acetate→70% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-d434718f11d44ed7ab2a82293717e48f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…