12-Hydroxydodecanoic Acid → HCID 66817916, compound

HRID 1755074Notes

Reaction equation

HRID 1755074 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O.[NH2:40][C:41]1([C:62]([NH2:64])=[O:63])[CH2:46][CH2:45][N:44]([S:47](/[CH:50]=[CH:51]/[C:52]2[C:57]([CH3:58])=[CH:56][C:55]([NH:59][CH3:60])=[CH:54][C:53]=2[CH3:61])(=[O:49])=[O:48])[CH2:43][CH2:42]1.C(N(C(C)C)CC)(C)C.CC(C)([O-])C.[K+]>CN(C=O)C.C(O)C>[CH3:58][C:57]1[CH:56]=[C:55]([NH:59][CH3:60])[CH:54]=[C:53]([CH3:61])[C:52]=1/[CH:51]=[CH:50]/[S:47]([N:44]1[CH2:43][CH2:42][C:41]2([N:40]=[C:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:39])[NH:64][C:62]2=[O:63])[CH2:46][CH2:45]1)(=[O:49])=[O:48]

Participants

8

Reactant 5

HCID 7903412-Hydroxydodecanoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23665647Potassium tert-butoxideHCID 66817982HCID 66817982, compound

Product 1

HCID 66817916HCID 66817916, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (57 mg, 0.149 mmol) was added to a solution of 12-hydroxy-dodecanoic acid (33 mg, 0.149 mol), 4-amino-1-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-piperidine-4-carboxylic amide (50 mg, 0.136 mmol) and diisopropylethylamine (71 μL, 0.47 mmol) in DMF (1.3 ml) at 0° C., and the mixture was stirred at room temperature for 1.5 hours. Ethanol (2.6 ml) and potassium t-butoxide (76 mg, 0.678 mmol) were added to the reaction mixture, and the mixture was heated with stirring at 70° C. for three hours. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution, and water was then added, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 8-[(E)-2-(2,6-dimethyl-4-methylamino-phenyl)-ethenesulfonyl]-2-(11-hydroxy-undecyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (58.7 mg, 79%).

Workup

  1. temperaturethe mixture was heated
  2. stirringwith stirring at 70° C. for three hours
  3. customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution, and water
  4. additionwas then added
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was sequentially washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-7d417ec43a0b46fc8612caac17c97e1e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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