HCID 86599513, compound → HCID 11307773, compound

HRID 1725254Notes

Reaction equation

HRID 1725254 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:41]=[CH:40][C:6]([CH2:7][N:8]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)[C:9](=[O:28])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1>C(#N)C.O.[Li+].[OH-]>[F:1][C:2]([F:42])([F:43])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:39])[F:38])=[CH:34][CH:35]=2)[C:9](=[O:28])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:40][CH:41]=1

Participants

5

Reactant 1

HCID 86599513HCID 86599513, compound

Product 1

HCID 11307773HCID 11307773, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3939Lithium HydroxideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl(2S)-3-[4-(2-{bis[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-2-ethoxypropanoate (0.662 g, 1.1 mmol) in acetonitrile (54 mL) was added aqueous 0.10 M LiOH (27 mL) and the solution was stirred at room temperature overnight. The solvent volume was reduced in vacuo and the remaining aqueous phase was diluted with water and aqueous 0.10 M LiOH (to a total volume of 300 mL, pH˜12) and washed with diethyl ether (2×100 mL). (The extraction process was complicated by the formation of emulsions.) The aqueous phase was acidified with 2 M HCl and extracted with ethyl acetate (3×100 mL). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo to afford 0.292 g (46%) of a colourless oil.

Workup

  1. washwashed with diethyl ether (2×100 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic phase was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b01a1cecff64328adaa4732c6f2e01f
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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