Citric Acid → HCID 86630856, compound

HRID 17485Notes

Reaction equation

HRID 17485 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[NH:11]1[CH2:14][CH:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12]1.Cl[C:24]1[O:25][C:26]2[C:27](=[C:29]([C:41]#[N:42])[C:30]([CH3:40])=[C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:32]=2[F:33])[N:28]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:41]([C:29]1[C:27]2[N:28]=[C:24]([N:11]3[CH2:14][CH:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:12]3)[O:25][C:26]=2[C:32]([F:33])=[C:31]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:30]=1[CH3:40])#[N:42]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 22101213tert-Butyl azetidin-3-ylcarbamate--hydrogen chloride (1/1)HCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 86630856HCID 86630856, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (787 μl, 4.63 mmol) and tert-butyl azetidin-3-ylcarbamate hydrochloride (483 mg, 2.31 mmol) were added to a dichloromethane (20 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (553 mg, 1.93 mmol), followed by stirring at room temperature for 30 minutes. With cooling with ice, aqueous 10% citric acid solution (10 ml) was added to the reaction liquid, followed by extraction with chloroform (50 ml), then the organic layer was washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to obtain the entitled compound (815 mg, 100%) as a colorless oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with chloroform (50 ml)
  3. washthe organic layer was washed with saturated brine (50 ml)
  4. dry with materialAfter drying over anhydrous sodium sulfate and concentration under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a5adbbcc827740eaaf7e3a26023c7ca7
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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