Ammonium Chloride → HCID 22293462, compound

HRID 966978Notes

Reaction equation

HRID 966978 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11]1([C:17]2([CH:27]=O)[CH2:26][CH2:25][C:20]3([O:24][CH2:23][CH2:22][O:21]3)[CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F:29][C:30]([F:56])([F:55])[C:31]1[CH:32]=[C:33]([CH2:41][CH2:42]S(C2SC3C=CC=CC=3N=2)(=O)=O)[CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1.[Cl-].[NH4+]>O1CCCC1.O>[C:11]1([C:17]2(/[CH:27]=[CH:42]/[CH2:41][C:33]3[CH:34]=[C:35]([C:37]([F:38])([F:40])[F:39])[CH:36]=[C:31]([C:30]([F:29])([F:55])[F:56])[CH:32]=3)[CH2:18][CH2:19][C:20]3([O:24][CH2:23][CH2:22][O:21]3)[CH2:25][CH2:26]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 122302758-phenyl-1,4-dioxaspiro[4,5]decane-8-carboxaldehydeHCID 22293456HCID 22293456, compound

Product 1

HCID 22293462HCID 22293462, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilazide (1M in tetrahydrofuran, 7.0 mL, 7.0 mmol) was added over 10 minutes to a cooled (−78° C.) solution of 8-phenyl-1,4-dioxaspiro[4,5]decane-8-carboxaldehyde (J. Med. Chem. 1975, 18, 593-599, 1.68 g, 6.8 mmol) and 2-({(2-[3,5-bis(trifluoromethyl)phenyl]ethyl}sulfonyl)benzothiazole (Description 34, 2.99 g, 6.8 mmol) in tetrahydrofuran (15 mL) and the mixture was stirred at −78° C. for 1 hour, then allowed to warm to room temperature. Aqueous ammonium chloride (saturated, 10 mL) was added and the mixture was stirred at room temperature for 30 minutes. Water (5 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic fractions were washed with brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (90:10) to give the tide compound as a pale yellow oil (2.43 g, 92%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic fractions were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with isohexane/EtOAc (90:10)

Sources & evidence

ORD record
ord-323412f03ef34f87bfe12838cf0ad47a
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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