Potassium sodium tartarate → HCID 59722595, compound

HRID 1664837Notes

Reaction equation

HRID 1664837 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C@@H:19]1[CH2:25][CH2:24][C@@H:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=2[F:33])[CH2:22][N:21]2[C:34]([CH2:37][C:38](OC)=[O:39])=[CH:35][N:36]=[C:20]12)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>ClCCl>[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[C@H:23]1[CH2:22][N:21]2[C:34]([CH2:37][CH2:38][OH:39])=[CH:35][N:36]=[C:20]2[C@H:19]([NH:18][C:16](=[O:17])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 86620128HCID 86620128, compound

Product 1

HCID 59722595HCID 59722595, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (1.0 M in hexanes; 3.77 mL, 3.77 mmol) was added to a solution of methyl [(6S,9R)-9-[(tert-butoxycarbonyl)amino]-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-3-yl]acetate (328 mg, 0.75 mmol) in dichloromethane (12 mL) at 0° C. After 1 h, saturated aqueous potassium sodium tartrate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→94% dichloromethane/methanol) gave the title compound (218 mg). MS 408.1 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→94% dichloromethane/methanol)

Sources & evidence

ORD record
ord-e952305af7d34847956bf498326ab58c
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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