Hydrochloric Acid → HCID 53825896, compound
Reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH2:23][CH3:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][CH:10]=1)(=[O:3])[CH3:2].Cl>C(OCC)(=O)C.CCOCC.C(O)C.[C].[Pd]>[C:1]([O:4][CH2:5][C:6]([NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])([CH2:23][CH3:24])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)(=[O:3])[CH3:2]Participants
Procedure
To a solution of 4-(4-benzyloxyphenyl)-2-tert-butoxycarbonylamino-2-ethylbutyl acetate (7 g) in ethyl acetate (80 ml) were added a 1 M solution of hydrochloric acid in ether (1 ml) and 10% palladium-carbon (0.4 g) and the suspension was subjected to catalytic reduction under an ordinary atmosphere at room temperature for 160 minutes. Catalyst was filtered off from the reaction mixture and the solvent was distilled away under reduced pressure. The residue obtained was dissolved in ethyl acetate (50 ml) and ethanol (50 ml). To the solution were added 10% palladium-carbon (0.4 g) and a 1 M solution of hydrochloric acid in ether (1 ml) and the suspension was subjected to catalytic reduction under an ordinary atmosphere at room temperature for 140 minutes. Catalyst was filtered off from the reaction mixture and the filtrate was concentrated under reduced pressure to give the subject compound (7.2 g).
Workup
- filtrationCatalyst was filtered off from the reaction mixture
- distillationthe solvent was distilled away under reduced pressure
- customThe residue obtained
- filtrationCatalyst was filtered off from the reaction mixture
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ac04bf1d820e4dc695d4b2d762a85e25
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05948820
Reaction notes
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