N-Methylbenzylamine → (S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

HRID 235534Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=O)[CH2:9][CH:10]=[CH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:38][NH:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C(OCC)(=O)C.C1COCC1>[CH2:40]([N:39]([CH3:38])[C:13](=[O:15])[C@@H:12]([N:8]([CH2:9][CH:10]=[CH2:11])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Conditions

Temperature: -22 °C

Procedure

Combine (S)-2-[N-(t-butoxycarbonyl)-allylamino-3-phenyl-propionic acid (11.1 g, 36.35 mmol), and THF (360 mL). Cool to -22° C. Add N-methylmorpholine (7.09 mL, 54.53 mmol) and then stir for 10 minutes. Add isobutyl chloroformate (7.09 mL, 54.53 mmol) and stir for 30 minutes at -22° C. Add N-methyl-N-benzylamine (7.09 mL, 54.53 mmol). Allow to warm to ambient temperature and stir for 2 hours. Dilute the reaction mixture with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph on silica gel eluting with 10% ethyl acetate/hexane to give the title compound.

Workup

temperatureAllow to warm to ambient temperature
extractionextract with water
customSeparate the layers
dry with materialdry the organic layer over MgSO4
filtrationfilter
customevaporate in vacuo

Sources & evidence

ORD record: ord-76178a063cb047afb67db9e8ecba3a0c
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05597845

Reaction notes

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