Diisopropylethylamine → Ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

HRID 1725216Notes

Reaction equation

HRID 1725216 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH2:8][CH3:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][C@H:15]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:16][C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([OH:25])=O)=[CH:19][CH:18]=1)[CH3:13].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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:8][CH3:9])[C:23](=[O:25])[CH2:22][O:21][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][C@H:15]([O:14][CH2:12][CH3:13])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:27][CH:26]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 580651N-Ethyl-4-chlorobenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11162260{4-[(2S)-2,3-Diethoxy-3-oxopropyl]phenoxy}acetic Acid

Product 1

HCID 68856731Ethyl(2S)-3-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(4-chlorobenzyl)-N-ethylamine (0.150 g, 0.88 mmol) and {4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid (0.270 g, 0.91 mmol) in methylene chloride (10 mL) were added N,N-diisopropylethylamine (0.34 mL, 1.9 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.320 g, 1.00 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was diluted with methylene chloride (40 mL) and the organic phase was washed with 5% HCl (50 mL), saturated aqueous NaHCO3 (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 methylene chloride/ethyl acetate 10:1 as the eluent yielded 0.24 g (61%) of a colourless oil.

Workup

  1. washthe organic phase was washed with 5% HCl (50 mL), saturated aqueous NaHCO3 (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 methylene chloride/ethyl acetate 10:1 as the eluent

Sources & evidence

ORD record
ord-80b06cd52db54ba0bd2486defbabf092
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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