2-Methyl-2-butene → HCID 178439230, compound

HRID 2090103Notes

Reaction equation

HRID 2090103 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:31]([CH3:33])[CH3:32])[C:6]2[O:10][C:9]([C:11]3[CH:29]=[CH:28][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][CH:26]=[O:27])[CH2:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:30]=1)#[N:2].CC(=CC)C.Cl([O-])=[O:40].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:31]([CH3:33])[CH3:32])[C:6]2[O:10][C:9]([C:11]3[CH:29]=[CH:28][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:20][CH2:21][C@H:22]([CH2:25][C:26]([OH:40])=[O:27])[CH2:23][CH2:24]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:30]=1)#[N:2]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 178439226HCID 178439226, compound

Product 1

HCID 178439230HCID 178439230, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension (partially dissolved) of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[trans-4-(2-oxoethyl)cyclohexyl]methyl}benzamide (50 mg, 0.113 mmol, EXAMPLE 43, Step B) in t-butanol (4 ml) was added 2-methyl-2-butene (0.060 ml, 0.570 mmol), and then a solution of sodium chlorite (25 mg, 0.276 mmol) and sodium dihydrogen phosphate (27 mg, 0.225 mmol) in water (1 ml). The mixture was stirred overnight at room temperature (the mixture remained a finely divided suspension), at which point LC/MS analysis showed no starting material. The mixture was diluted with 10 ml of water and 10 ml of ethyl acetate. The phases were separated and the aqueous phase was acidified to pH 4 and extracted with 2×10 ml of ethyl acetate. The combined organics were washed with 10 ml of brine, dried (sodium sulfate), and concentrated to provide the title compound (52 mg, 0.113 mmol, 100% yield). Mass spectrum (ESI) 459.8 (M+1).

Workup

  1. customThe phases were separated
  2. extractionextracted with 2×10 ml of ethyl acetate
  3. washThe combined organics were washed with 10 ml of brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2cd664d6e724b3f9a424a43bfe4ed7b
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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