Methyl chloroformate → HCID 131731842, compound

HRID 74472Notes

Reaction equation

HRID 74472 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:20][SiH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].Cl[C:47]([O:49][CH3:50])=[O:48].[Cl-].[NH4+]>O1CCCC1>[CH3:50][O:49][C:47]([C:11]1[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:18]2[C:13]([CH:12]=1)=[CH:14][CH:15]=[C:16]([C:19]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[O:20][SiH2:21][C:22]([CH3:24])([CH3:25])[CH3:23])[CH:17]=2)=[O:48]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 131731843HCID 131731843, compound

Product 1

HCID 131731842HCID 131731842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

An anhydrous tetrahydrofuran (THF) solution (20 ml) of crude 1-benzenesulfonyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-1H-indole was cooled to −78° C., and a prepared tetrahydrofuran (THF) solution of lithium diisopropyl amide (LDA) was added thereto. This was stirred at −78° C. for 30 minutes. Methyl chloroformate (0.43 ml, 5.98 mmol) was added thereto, and this was stirred at −78° C. for 30 minutes. An aqueous solution saturated with ammonium chloride was added to the reaction mixture, and this was warmed to room temperature. After ethyl acetate extraction, the organic layer was dried over anhydrous sodium sulfate. The desiccant was removed by filtration and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=98/2 to 4/1). Thus, 1-benzenesulfonyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-1H-indole-2-carboxylic acid methyl ester was obtained as a brown amorphous material (882 mg, 51%).

Workup

  1. stirringthis was stirred at −78° C. for 30 minutes
  2. temperaturethis was warmed to room temperature
  3. extractionAfter ethyl acetate extraction
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration and concentration
  6. customThen, the residue obtained by concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=98/2 to 4/1)

Sources & evidence

ORD record
ord-3d9690deaf21401c82989bd10b89b2ae
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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