Potassium sodium tartarate → HCID 59722591, compound

HRID 1664840Notes

Reaction equation

HRID 1664840 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(C)C)=[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][CH:38]=[O: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 21225700Diisobutylaluminumhydride2×HCID 86620129HCID 86620129, compound

Product 1

HCID 59722591HCID 59722591, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (1.0 M in dichloromethane; 0.81 mL, 0.807 mmol) was added to a solution of isopropyl [(6S,9R)-9-[(tert-butoxycarbonyl)amino]-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-3-yl]acetate (187 mg, 0.403 mmol) in dichloromethane (10 mL) at −78° C. After 1 h, an additional amount of diisobutylaluminum hydride (0.81 mL, 0.807 mmol) was added. After 2.5 h, saturated aqueous potassium sodium tartrate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (120 mg). MS 406.2 (M+1).

Workup

  1. waitAfter 2.5 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-1d8484264b444147b999fd0b905ad7ca
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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