2-Methoxyphenethylamine → (S)-N-(2-Methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

HRID 235535Notes

Reaction equation

HRID 235535 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][CH:21]=[CH2:22])[C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[CH2:27]CN.Cl.[CH3:35][N:36](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)(=O)C>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[CH2:27][N:36]([CH3:35])[C:10](=[O:12])[C@@H:9]([N:8]([CH2:20][CH:21]=[CH2:22])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 748962-MethoxyphenethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12944586HCID 12944586, compound

Product 1

HCID 86750260(S)-N-(2-Methoxybenzyl)-N-methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine (S)-2-[N-(t-butoxycarbonyl)-allylamino]-3-phenyl-propioic acid (1.59 g, 5.20 mmol), (2-methoxybenzyl)methylamine (0.79 g, 5.20 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.12 g, 5.72 mmol), 1-hydroxybenzotriazole (0.38 g, 2.52 mmol ), and diisopropylethylamine (1.34 mL, 6.5 mmol) in dichloromethane (50 mL)and stir for 18 hours. Dilute with ethyl acetate and extract with 1M hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. Dry the separated organic layer over MgSO4, filter and evaporate in vacuo. Chromatograph on silica gel eluting sequentially with 5% ethyl acetate/hexane and 10% ethyl acetate/hexane to give the title compound: TLC Rf =0.55 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. extractionextract with 1M hydrochloric acid
  2. dry with materialDry the separated organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-bd58e1994f3a489e96644bbfabb06e1b
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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