Hydrochloric Acid → HCID 19348428, compound

HRID 1418175Notes

Reaction equation

HRID 1418175 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][Si](C(C)(C)C)(C)C)=[CH:8][C:7]=1[NH:21][C:22](=[O:40])[CH2:23][CH:24]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][CH3:39])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH3:5])([CH3:4])[CH3:3]>CO.C(Cl)Cl.C(OCC)C>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[NH:21][C:22](=[O:40])[CH2:23][CH:24]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][CH3:39])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH3:3])([CH3:4])[CH3:5]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 19348806HCID 19348806, compound

Product 1

HCID 19348428HCID 19348428, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

0.1 ml of concentrated aqueous hydrochloric acid was added, with stirring and ice-cooling, to a solution of 460 mg (0.828 mmol) of N-[2-t-butyl-5-(t-butyldimethylsilyloxymethyl)phenyl]-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Preparation 8) in a mixture of 9 ml of methanol and 1 ml of methylene chloride, and the resulting mixture was allowed to stand at the same temperature for 40 minutes, after which it was diluted with diethyl ether. The diluted solution was washed twice with water and once with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was recrystallized from a mixture of hexane and ethyl acetate to give 353 mg (yield 96%) of the title compound as crystals, melting at 125°-126° C.

Workup

  1. washThe diluted solution was washed twice with water and once with a saturated aqueous solution of sodium chloride
  2. dry with materialafter which it was dried over anhydrous sodium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe resulting residue was recrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-173b92a844704ad2b6378ae3a405efb4
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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