Triethylamine → Carbamic acid, N-[3-[[2-(3-methoxyphenyl)ethyl]amino]-3-oxopropyl]-, 1,1-dimethylethyl ester

HRID 2284100Notes

Reaction equation

HRID 2284100 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][C:22](O)=[O:23])=[O:18])([CH3:15])([CH3:14])[CH3:13].OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C(N=C=NCCCN(C)C)C>O.C(OCC)(=O)C.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH:8][C:22](=[O:23])[CH2:21][CH2:20][NH:19][C:17](=[O:18])[O:16][C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 748663-MethoxyphenethylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 178418300HCID 178418300, compound

Product 1

HCID 86673951Carbamic acid, N-[3-[[2-(3-methoxyphenyl)ethyl]amino]-3-oxopropyl]-, 1,1-dimethylethyl esterYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-methoxyphenethylamine (Aldrich, 100 mg, 0.66 mmol), 3-((tert-butoxycarbonyl)amino)-propanoic acid (125 mg, 0.66 mmol), hydroxybenzotriazole (8.9 mg, 0.066 mmol), triethylamine (102 μL, 0.73 mmol) and dimethyformamide (6.6 mL) were combined, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (139 mg, 0.73 mmol) was added. The solution was allowed to stir at room temperature overnight. Upon completion, ethyl acetate and water were added and the layers were separated. The aqueous phase was extracted with ethyl acetate then the combined organic layers were washed with brine and dried over Na2SO4. Solvent was removed under reduced pressure to give crude product which was purified by flash chromatography using 0-80% ethyl acetate/hexane as the eluent to give the product as a pure white solid (140 mg, 66%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed under reduced pressure
  6. customto give crude product which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-7cce825e05de48159018361342e08755
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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