Hydrochloric Acid → HCID 57148696, compound
Reaction equation
[C:1]([C@H:9]([CH:32]([CH3:34])[CH3:33])[CH2:10][C@@H:11]1[O:15]C(C)(C)[N:13](C(OC(C)(C)C)=O)[C@H:12]1[CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=[O:8])C1C=CC=CC=1.Cl.C(OC)(OC)OC.[C:43]1(C)[CH:48]=[CH:47][C:46](S(O)(=O)=O)=[CH:45][CH:44]=1.[C:54](=O)(O)[O-].[Na+]>CO>[CH:26]1([CH2:25][C@@H:12]([C@@H:11]2[CH2:10][C@@H:9]([CH:32]([CH3:33])[CH3:34])[C:1]([O:8][CH3:54])([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:15]2)[NH2:13])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1Participants
Procedure
400 mg (0.85 mmol) of t-butyl (4S,5S)-5-[(S)-2-benzoyl-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate are dissolved in 15 ml of methanol and treated with 4.7 ml (18 mmol) of 3.9M hydrochloric acid in methanol. The reaction mixture is thereafter stirred at room temperature for 20 hours and subsequently evaporated under reduced pressure. The residue is dissolved in 5 ml of methanol and the solution is treated with 0.2 ml (1.8 mmol) of trimethyl orthoformate and a few crystals of p-toluenesulphonic acid and stirred at room temperature for 2 hours and at 50° for 2 hours. Thereafter, the reaction mixture is poured into 2N sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extracts are dried over magnesium sulphate and evaporated under reduced pressure, whereby there is obtained 0.27 g of (αS,2S,4S)-α-(cyclohexylmethyl)tetrahydro-4-isopropyl-5-methoxy-5-phenyl-2-furanmethanamine as an oil, MS: 313 (M-CH3OH)+.
Workup
- customsubsequently evaporated under reduced pressure
- dissolutionThe residue is dissolved in 5 ml of methanol
- extractionextracted with methylene chloride
- dry with materialThe methylene chloride extracts are dried over magnesium sulphate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-9e48e3e57e394064b07fd0494fe6bea8
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05140011
Reaction notes
Loading…