Hydrochloric Acid → HCID 68597601, compound

HRID 1911292Notes

Reaction equation

HRID 1911292 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 paritioned 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. extractionthe organic layer was extracted with water (50 mL)
  3. extractionextracted with dichloromethane (2×40 mL)
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53b844d7022c4fc88e227b9e1981209b
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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