Hydrochloric Acid → HCID 68597601, compound

HRID 1913307Notes

Reaction equation

HRID 1913307 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>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67360794HCID 67360794, compound

Product 1

HCID 68597601HCID 68597601, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 h, complete deprotection observed by LCMS. The reaction mixture was cooled, stirred for 8 h, then diluted with methyl tert-buthy ether (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% yield). 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-98064c737cbd4ce2b815cc76dad07155
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

Loading…