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

HRID 235534
Notes
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Reaction equation

HRID 235534 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 12944585N-(t-butoxycarbonyl)-allylamino-3-phenyl-propionic acid

Product 1

HCID 54096526(S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

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

  1. temperatureAllow to warm to ambient temperature
  2. extractionextract with water
  3. customSeparate the layers
  4. dry with materialdry the organic layer over MgSO4
  5. filtrationfilter
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes