Acetic Acid → HCID 59003224, compound

HRID 2353931Notes

Reaction equation

HRID 2353931 reaction equation
C(O)(=O)C.C(=O)C.[CH:8]([O:11][C:12]([N:14]1[CH2:20][CH2:19][CH2:18][CH:17]([N:21]([C:37](=O)[CH3:38])[CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[C:16]2[CH:40]=[CH:41][C:42]([Cl:44])=[CH:43][C:15]1=2)=[O:13])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O>[CH:8]([O:11][C:12]([N:14]1[CH2:20][CH2:19][CH2:18][CH:17]([N:21]([CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:35])([F:34])[F:36])[CH:24]=2)[CH2:37][CH3:38])[C:16]2[CH:40]=[CH:41][C:42]([Cl:44])=[CH:43][C:15]1=2)=[O:13])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11489735HCID 11489735, compound

Product 1

HCID 59003224HCID 59003224, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add acetic acid (0.05 mL, 0.078 mmol) and acetaldehyde (34 mg, 0.78 mmol) to a solution of 5-(3,5-Bis-trifluoromethyl-benzylamino)-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (see example 3) (40 mg, 0.078 mmol) in dimethylformamide (1 mL). Stir at room temperature for 2 h. Add sodium triacetoxyborohydride (33 mg, 0.16 mmol) and stir the mixture at room temperature for 2 h. Add saturated solution of sodium bicarbonate and extract with ethyl acetate (3×10 mL). Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Chromatograph the residue over silica cartridge, eluting with hexanes/ethyl acetate (10:1), to afford the title compound (11 mg, 26%). MS (ES+): 537 (M+H).

Workup

  1. extractionAdd saturated solution of sodium bicarbonate and extract with ethyl acetate (3×10 mL)
  2. dry with materialDry the organic layer over anhydrous sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. washChromatograph the residue over silica cartridge, eluting with hexanes/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-ec1f4974fe484a0999697a0caf4558bb
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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