1-Hydroxybenzotriazole → (S)-N-Methyl-2-[N'-(t-butoxycarbonyl)-allylamino]-3-phenyl-propionamide

HRID 235542Notes

Reaction equation

HRID 235542 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](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:24][N:25](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.CN.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)(=O)C>[CH3:24][NH:25][C:10](=[O:11])[C@@H:9]([N:8]([CH2:20][CH:21]=[CH2:22])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 12944586HCID 12944586, compound

Product 1

HCID 86750266(S)-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-propionic acid (0.7 g, 2.29 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.50 g, 2.52 mmol), 1-hydroxybenzotriazole (0.38 g, 2.52 mmol), methylamine hydrochloride (0.17 g, 2.52 mmol) and diisopropylethylamine (0.59 mL, 2.52 mmol) in dichloromethane (23 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% methanol/dichloromethane and 10% methanol/dichloromethane to give the title compound: TLC Rf =0.44 (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-74ca55db7f834755a9fce873798c8fe8
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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