Hydrochloric Acid → HCID 68555825, compound

HRID 2370302Notes

Reaction equation

HRID 2370302 reaction equation
C1O[C:4]2([CH2:11][CH2:10][CH:9]3[CH2:12][CH:5]2[CH2:6][CH2:7][CH:8]3[NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[O:3]C1.Cl>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[NH:13][CH:8]1[CH2:7][CH2:6][CH:5]2[CH2:12][CH:9]1[CH2:10][CH2:11][C:4]2=[O:3])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72238040HCID 72238040, compound

Product 1

HCID 68555825HCID 68555825, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

915 mg of 6-Benzyloxycarbonylamino-bicyclo[3.3.1]nonan-2-one ethylene ketal (99) were suspended in 7.6 mL of acetone and 2.9 mL of 5N HCl were added. The mixture was stirred for 2 h, the acetone was evaporated and the remaining liquid was slowly added to sat. NaHCO3. The aqueous layer was extracted with dichloromethane three times. The combined organic layer was dried over sodium sulfate and evaporated to dryness to give 0.79 g of the desired product. Rt=2.87 min (Method E). Detected mass: 288.2 (M+H+).

Workup

  1. customthe acetone was evaporated
  2. additionthe remaining liquid was slowly added to sat. NaHCO3
  3. extractionThe aqueous layer was extracted with dichloromethane three times
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-badaaf2e0ecd420b93b62776ea8ec672
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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