Tetrahydrofuran → HCID 86618879, compound

HRID 252397Notes

Reaction equation

HRID 252397 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].O1CCCC1.[CH:18]([CH:20]([NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:21][CH:22]([CH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[CH:31]=[C:30]2[CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:23]([CH3:25])[CH3:24])=[O:19]>CS(C)=O>[CH3:41][O:40][CH2:39][CH2:38][CH2:37][C:30]1[C:29]2[C:33](=[CH:34][CH:35]=[C:27]([CH2:26][CH:22]([CH:23]([CH3:24])[CH3:25])[CH2:21][CH:20]([NH:42][C:43](=[O:49])[O:44][C:45]([CH3:47])([CH3:46])[CH3:48])[CH:18]3[CH2:7][O:19]3)[CH:28]=2)[N:32]([CH3:36])[CH:31]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 86618880HCID 86618880, compound

Product 1

HCID 86618879HCID 86618879, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

1.29 g of trimethylsulphoxonium iodide and 0.66 g of potassium tert-butoxide are stirred under high vacuum overnight, admixed with 8 ml of tetrahydrofuran and subsequently cooled to 0° C. A solution of 1.01 g of tert-butyl {1-formyl-3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methylpentyl}carbamate in 8 ml of dimethyl sulphoxide is added dropwise. On completion of reaction (TLC monitoring), the reaction mixture is partitioned between water and tert-butyl methyl ether, and the aqueous phase is extracted once more with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water (3×) and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. customOn completion of reaction (TLC monitoring)
  2. customthe reaction mixture is partitioned between water and tert-butyl methyl ether
  3. extractionthe aqueous phase is extracted once more with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed successively with water (3×) and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4864716cc5ce432f9ef8a496cee439b7
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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