Tetrahydrofuran → HCID 59722653, compound

HRID 1664860Notes

Reaction equation

HRID 1664860 reaction equation
[CH2:1]([Mg]Br)C.C([C:8]1[N:12]2[CH2:13][C@H:14]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=3[F:33])[CH2:15][CH2:16][C@@H:17]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]2=[N:10][CH:9]=1)(=O)C.[O:34]1[CH2:38][CH2:37][CH2:36]C1>>[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[C@H:14]1[CH2:13][N:12]2[C:8]([C:38]([OH:34])([CH3:1])[CH2:37][CH3:36])=[CH:9][N:10]=[C:11]2[C@H:17]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 59722739HCID 59722739, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59722653HCID 59722653, compound

Procedure

Ethylmagnesium bromide (3.0 M in ether; 82.0 μL, 0.247 mmol) was added to a solution of tert-butyl (6S,9R)-3-acetyl-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (25 mg, 0.062 mmol) in tetrahydrofuran (1 mL) at 0° C. After 10 min, the reaction mixture was quenched with water and the mixture was extracted with dichloromethane (3×). The organic layer was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→60% dichloromethane/ethyl acetate) gave the title compound (17 mg). MS 436.2 (M+1).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionthe mixture was extracted with dichloromethane (3×)
  3. washThe organic layer was washed with water, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→60% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-ccaf0bce693946658fe542b7b150f7b5
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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