Ammonium Chloride → HCID 18974022, compound

HRID 2395047Notes

Reaction equation

C([O:5][C:6]([C:8]1[C:9](=[O:15])[NH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:7])(C)(C)C.C([N-]C(C)C)(C)C.[Li+].[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38]CCC1C=CC(C(O)=O)=CC=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>C1COCC1>[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][CH2:14][C:11]1[NH:10][C:9](=[O:15])[C:8]([C:6]([OH:5])=[O:7])=[CH:13][CH:12]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: -30 °C

Procedure

3-tertbutoxycarbonyl-6-methyl-2(1 H)-pyridinone (1.49 g, J. Het. Chem., 1981, 18, 1611) was added to a THF (20 ml) solution of lithium diisopropylamide (14.3 mmol, prepared by the standard method) and stirred under argon, at -30° C., for 2.5 hours. 2-Benzyloxybenzyl bromide (2 g, prepared as described in Example 1) in THF (10 ml) was added and the mixture stirred, at -30° C., for 1 hour, then warmed to ambient temperature. The mixture was poured into saturated aqueous ammonium chloride (200 ml) and extracted with dichloromethane. The solvent was evaporated and crystallised from isopropranol. There was thus obtained 6-(2-[2-benzyloxyphenyl)ethyl]-3-tertbutoxycarbonyl-2(1 H)-pyridinone (1.85 g) m.p. 146°-147° C.

Workup

customprepared by the standard method) and
stirringthe mixture stirred, at -30° C., for 1 hour
temperaturewarmed to ambient temperature
extractionextracted with dichloromethane
customThe solvent was evaporated
customcrystallised from isopropranol

Sources & evidence

ORD record: ord-a9dab69428414a8e929d597df5fa53ab
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811459

Reaction notes

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