Hydrochloric Acid → HCID 58380956, compound

HRID 45187Notes

Reaction equation

HRID 45187 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([C:12]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:21][CH2:20][C:15]2(OCC[O:16]2)[CH2:14][CH2:13]1)[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([C:12]1([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]1)[CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58381041HCID 58381041, compound

Product 1

HCID 58380956HCID 58380956, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.22 g of {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-butyl}-carbamic acid tert-butyl ester (16) were dissolved in 42 mL of acetone and 3 mL of 1N hydrochloric acid were added. The mixture was stirred at room temperature until conversion was complete. 40 mL of saturated aqueous sodium bicarbonate solution were added and the reaction mixture was extracted with ethyl acetate three times. The combined organic layer was extracted with brine, dried over sodium sulphate and evaporated to dryness to give 966 mg of crude (17), that was sufficiently pure for further conversion. Rt=1.72 min (Method 5). Detected mass: 308.2 (M-Isobutene+H+).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate three times
  2. extractionThe combined organic layer was extracted with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7691bddd16e648ebabf5bf4fb0c0be6f
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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