2,2,2-Trifluoroethanol → 2-ethoxy-3-(4-{2-[N-heptyl-N-(2,2,2-trifluoroethoxycarbonyl)amino]ethoxy}phenyl)propionic Acid Ethyl Ester

HRID 1744463Notes

Reaction equation

HRID 1744463 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)[CH3:2].Cl[C:29](Cl)([O:31][C:32](=[O:38])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[F:47][C:48]([F:52])([F:51])CO>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:32]([O:31][CH2:29][C:48]([F:52])([F:51])[F:47])=[O:38])=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 8471TriethylamineHCID 94429TriphosgeneHCID 696257582-Ethoxy-3-[4-(2-heptylaminoethoxy)phenyl]propionic acid ethyl ester

Product 1

HCID 696256122-ethoxy-3-(4-{2-[N-heptyl-N-(2,2,2-trifluoroethoxycarbonyl)amino]ethoxy}phenyl)propionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound obtained in Example 1, Step e (75.9 mg) in methylene chloride (2 ml) was added with triphosgene (89 mg, Tokyo Kasei Kogyo) and triethylamine (140 μl) and stirred for 2 hours under ice cooling. The reaction mixture was added with 2,2,2-trifluoroethanol (47 μl, Tokyo Kasei Kogyo) and stirred for three days. The reaction mixture was diluted with methylene chloride, washed with 1 N HCl and saturated aqueous sodium hydrogencarbonate in this order, dried over magnesium sulfate and concentrated. The obtained residue was applied to a silica gel column and eluted with hexane/ethyl acetate (5:1) to obtain the title compound (48.5 mg).

Workup

  1. stirringstirred for three days
  2. washwashed with 1 N HCl and saturated aqueous sodium hydrogencarbonate in this order
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-0ae33dc22b454e9dbc78eef3fe5c1a70
Source dataset
uspto-grants-2006_03
Patent number
US07015345B2

Reaction notes

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