Diisopropylethylamine → ethyl(2S)-2-ethoxy-3-[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]propanoate

HRID 1725222Notes

Reaction equation

HRID 1725222 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)[CH3:2].[CH2:15]([O:17][C@H:18]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][C:26]([OH:28])=O)=[CH:22][CH:21]=1)[CH3:16].C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH2:15]([O:17][C@@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=2)=[O:28])=[CH:29][CH:30]=1)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 485421Benzenemethanamine, N-ethyl-4-(trifluoromethyl)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11162260{4-[(2S)-2,3-Diethoxy-3-oxopropyl]phenoxy}acetic Acid

Product 1

HCID 68856704ethyl(2S)-2-ethoxy-3-[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]propanoateYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-ethyl-N-[4-(trifluoromethyl)benzyl]amine (0.213 g, 1.05 mmol) and {4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid (0.296 g, 1.00 mmol) in methylene chloride (10 mL) were added N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.337 g, 1.05 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was diluted with methylene chloride (90 mL) and the organic phase was washed with 5% HCl (2×50 mL), saturated aqueous NaHCO3 (2×50 mL), and brine (50 mL), dried over Na2SO4, and concentrated in vacuo. Purification on a prepacked column of silica gel (Isolute® SPE Column, 50 g/150 mL) with methanol (0-1% gradient) in methylene chloride as the eluent yielded 0.339 g (70%) of a colourless oil.

Workup

  1. washthe organic phase was washed with 5% HCl (2×50 mL), saturated aqueous NaHCO3 (2×50 mL), and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification on a prepacked column of silica gel (Isolute® SPE Column, 50 g/150 mL) with methanol (0-1% gradient) in methylene chloride as the eluent

Sources & evidence

ORD record
ord-abd58b8921fb47be9b040a651cd53101
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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