Diisopropylethylamine → HCID 21034893, compound

HRID 1833246Notes

Reaction equation

HRID 1833246 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:19])[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:7][NH2:8])[CH3:3].[CH:20]([O:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32](O)=[O:33])[CH:28]=[CH:29][CH:30]=1)([CH2:22][CH3:23])[CH3:21].CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[CH2:2]([O:4][C:5](=[O:19])[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:7][NH:8][C:32](=[O:33])[CH2:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH:20]([CH2:22][CH3:23])[CH3:21])[CH:26]=1)[CH3:3]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22048444HCID 22048444, compoundHCID 69551005HCID 69551005, compound

Product 1

HCID 21034893HCID 21034893, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirred solution 3-amino-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester hydrochloride (6.5 g, 25.8 mmol) and (3-sec-butoxy-phenyl)-acetic acid (5.9 g, 28.4 mmol) in N,N-dimethylformamide (130 mL) was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium hexaflurophosphate (HBTU) (11.8 g, 31.1 mmol) and diisopropylethylamine (14.8 mL, 85.0 mmol). The reaction mixture was stirred at room temperature for 15 hrs. The solvent was evaporated and the residue was diluted with ethyl acetate and saturated sodium bicarbonate solution. The aqueous phase was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with 1N hydrogen chloride solution (50 mL), water (50 mL), saturated aqueous sodium chloride solution (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane, 100% ethyl acetate) afforded 3-[2-(3-sec-butoxy-phenyl)-acetylamino]-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (11.2 g, 98% yield) as a red oil.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ethyl acetate and saturated sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
  4. washThe combined extracts were washed with 1N hydrogen chloride solution (50 mL), water (50 mL), saturated aqueous sodium chloride solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c0ab5006974446ea9574d1fb2aa6926
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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