Hydrochloric Acid → HCID 10140000, compound

HRID 584993Notes

Reaction equation

HRID 584993 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:17][CH:16]=2)=[CH:13][C:12]([CH2:29][N:30]([CH3:40])[C:31](=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:11][CH:10]=1)C1C=CC=CC=1.I[Si](C)(C)C.Cl.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C.C(#N)C>[O:27]=[C:25]1[NH:24][C:23](=[O:28])[CH:22]([CH2:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]3[C:9]([OH:8])=[CH:10][CH:11]=[C:12]([CH2:29][N:30]([CH3:40])[C:31](=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:13]=3)=[CH:20][CH:19]=2)[S:26]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 2724141Tetrabutylammonium FluorideHCID 10303068HCID 10303068, compound

Product 1

HCID 10140000HCID 10140000, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

250 mg (0.45 mmol) of N-[6-benzyloxy-4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methyloctanamide, 4 ml of acetonitrile and 130 mg (0.65 mmol) of iodotrimethylsilane are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is heated, at 50° C. for 3 hours. At room temperature, 450 μl of 1N hydrochloric acid and 450 μl of tetrabutylammonium fluoride are added. The medium is then diluted with ethyl acetate and washed with sodium thiosulfate solution. After separation of the phases once settling has taken place, the organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an ethyl acetate/heptane mixture (6/4). 150 mg (72%) of N-[4′-(2,4-dioxo-thiazolidin-5-ylmethyl)-6-hydroxybiphenyl-3-ylmethyl]-N-methyloctanamide are obtained in the form of a yellowish foam.

Workup

  1. washwashed with sodium thiosulfate solution
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with an ethyl acetate/heptane mixture (6/4)

Sources & evidence

ORD record
ord-e3fa3ad8141042ea947d90a719266bd8
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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