Hydrochloric Acid → HCID 86698456, compound

HRID 527647Notes

Reaction equation

HRID 527647 reaction equation
[CH3:1][C:2]1([CH3:33])[C:6]2[C:7]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH:19][C:20]([C@H:22]([NH:25]C(=O)OC(C)(C)C)[CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=3)=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=2[O:4][CH2:3]1.Cl.C(O)(C)C.C([O-])(O)=O.[Na+]>C(OC(C)C)(=O)C>[NH2:25][C@H:22]([CH2:23][CH3:24])[C:20]([NH:19][C:16]1[CH:17]=[N:18][C:13]([O:12][C:7]2[C:6]3[C:2]([CH3:1])([CH3:33])[CH2:3][O:4][C:5]=3[C:10]([CH3:11])=[CH:9][CH:8]=2)=[CH:14][CH:15]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 86698454HCID 86698454, compound2×

Product 1

HCID 86698456HCID 86698456, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

The 1,1-dimethylethyl {(1R)-1-[({6-[(3,3,7-trimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]propyl}carbamate (Intermediate 187, 480 mg, 1.05 mmol) was dissolved in iso-propyl acetate (5 mL) and HCl 5-6N in isopropanol (1 ml, 5.25 mmol) was added. The solution was stirred at room temperature for 1 hour and then heated to ˜50-55° C. until complete conversion. The mixture was cooled to room temperature and treated with an aqueous saturated solution of NaHCO3. Two phases were separated and the organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol 95:5 as eluents affording the title compound (0.31 g) as yellowish foam.

Workup

  1. temperatureheated to ˜50-55° C. until complete conversion
  2. temperatureThe mixture was cooled to room temperature
  3. customTwo phases were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-dff15bcfe95b4713bf3b88ab11b5052a
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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