Hydrochloric Acid → HCID 66691681, compound

HRID 1773660Notes

Reaction equation

HRID 1773660 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([B:12]3[O:16]C(C)(C)C(C)(C)[O:13]3)=[CH:8][C:7]=2[CH3:21])CC1.I([O-])(=O)(=O)=O.[Na+].Cl>CC(C)=O>[CH3:21][C:7]1[CH:8]=[C:9]([B:12]([OH:16])[OH:13])[CH:10]=[CH:11][C:6]=1[C:5](=[O:22])[NH:4][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 66691012HCID 66691012, compound

Product 1

HCID 66691681HCID 66691681, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 20.22 g (67 mmol) N-cyclopropyl-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide in acetone (300 mL) were added 43.08 g (201 mmol) sodium periodate 134 mL ammonium acetate (134 mmol, 1M in water) and the mixture was stirred for 3 h at rt and 2 h at 40° C. 4 N HCl was added (32 mL) and the organic phase was removed in vaccuo. The mixture was extracted with ethyl acetate, and the organic phase was washed with water, dried and removed in vaccuo to yield 14.59 g (94.2%) of the title compound. 1H-NMR (400 MHz, DMSO-d6), δ [ppm]=0.44-0.52 (2H), 0.59-0.67 (2H), 2.26 (3H), 2.78 (1H), 7.18 (1H), 7.53-7.61 (2H), 8.01 (2H), 8.19 (1H).

Workup

  1. customthe organic phase was removed in vaccuo
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. customdried
  5. customremoved in vaccuo

Sources & evidence

ORD record
ord-33525c6c67a840e3bda57380706b9c99
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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