Tributylphosphine → HCID 68855304, compound

HRID 1785243Notes

Reaction equation

HRID 1785243 reaction equation
[I:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:17](O)[CH3:18].[CH3:20][O:21][C:22](=[O:33])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][C:26]=1[CH3:32].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH3:20][O:21][C:22](=[O:33])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][CH:17]([C:3]2[S:4][C:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)=[CH:6][C:2]=2[I:1])[CH3:18])=[CH:27][C:26]=1[CH3:32]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 541446143-(4-Mercapto-2-methyl-phenyl)-propionic Acid Methyl EsterHCID 57594992HCID 57594992, compound

Product 1

HCID 68855304HCID 68855304, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 1-[3-Iodo-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanol (1.52 g, 3.96 mmole) and 3-(4-Mercapto-2-methyl-phenyl)-propionic acid methyl ester (0.769 g, 3.96 mmole) in toluene (20 mL) at room temperature, is added tributylphosphine (1.98 mL, 7.92 mmole) followed by a solution of 1,1′-(azodicarbonyl)-dipiperidine (1.99 g, 7.92 mmole) in toluene (20 mL). The reaction is stirred overnight, and then diluted with hexane (100 mL). The precipitate is removed through filtration and the filtrate is concentrated, loaded to a silica gel column, eluted with ethyl acetate in hexane (0-15%) and concentrated to provide the titled compound as yellow solid.

Workup

  1. customThe precipitate is removed through filtration
  2. concentrationthe filtrate is concentrated
  3. washeluted with ethyl acetate in hexane (0-15%)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-618470c700bc4ec5b8d4465d4eb4b009
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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