Hydrochloric Acid → HCID 68597601, compound

HRID 536454Notes

Reaction equation

HRID 536454 reaction equation
[Cl:1][C:2]1[C:3]([F:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C@H:7]2[NH:14]C(=O)OC(C)(C)C.CO.Cl>CC(OC)(C)C.O>[Cl:1][C:2]1[C:3]([F:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:12])([CH3:13])[CH2:8][C@H:7]2[NH2:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67360794HCID 67360794, compound

Product 1

HCID 68597601HCID 68597601, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

The crude (R)-tert-butyl 8-chloro-7-fluoro-2,2-dimethylchroman-4-ylcarbamate (4.47 g, 13.5 mmol), MeOH (36 mL), and concentrated HCl (4 mL) were heated to 50° C. After 2 hours, complete deprotection was observed by LCMS. The reaction mixture was cooled, stirred for 8 hours, and then diluted with MTBE (60 mL) and water (40 mL). The mixture was partitioned and the organic layer was extracted with water (50 mL). The aqueous layer was basified with 2N NaOH (40 mL) and extracted with dichloromethane (2×40 mL). The organic extracts were dried (Na2SO4), filtered, and concentrated to give the title compound (2.87 g, 12.50 mmol, 92%). MS (ESI+) m/z 230 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe mixture was partitioned
  3. extractionthe organic layer was extracted with water (50 mL)
  4. extractionextracted with dichloromethane (2×40 mL)
  5. dry with materialThe organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-51cb2712477b4402babba168d55a2eb1
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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