Methyl chloroformate → Methyl 2-[[(1,1-Dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate

HRID 828

反応式

HRID 828 の反応式
[CH3:1][C:2]([NH:5][S:6]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.Cl[C:21]([O:23][CH3:24])=[O:22]>C1COCC1.C(OCC)(=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][C:13]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])=[O:7])([CH3:1])[CH3:3]

参加物

6

反応物 3

HCID 6586Methyl chloroformateHCID 19693810N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-2-sulfonamideHCID 178418339Butyllithium

生成物 1

HCID 19693824Methyl 2-[[(1,1-Dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate収率 14.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2.5 g (11.5 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-2-sulfonamide in 50 mL THF under nitrogen atmosphere cooled to below -70° C. was added dropwise 13 mL (32.5 mmol) of 2.5M n-butyllithium at such a rate as to keep the temperature below -58° C. After stirring at -20° C. to -10° C. for 30 min then 1 h at 0° C., the mixture was recooled to -70° C. and treated with a solution of 1.63 g (17.3 mmol) of methyl chloroformate in 6 mL THF causing an exotherm to -57° C. The reaction mixture was stirred overnight at ambient temperature then diluted with 200 mL of ethyl acetate. This solution was washed successively with two 60 mL portions of 1N HCl, brine, then dried (Na2SO4) and evaporated to a dark oil. The crude product was purified by chromatography on silica gel (30% ethyl acetate/70% hexanes) then collected from hexanes to afford 0.45 g of the title compound, m.p. 105°-108° C.

後処理

  1. customthe temperature below -58° C
  2. custom1 h
  3. customat 0° C.
  4. customwas recooled to -70° C.
  5. stirringThe reaction mixture was stirred overnight at ambient temperature
  6. washThis solution was washed successively with two 60 mL portions of 1N HCl, brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated to a dark oil
  9. customThe crude product was purified by chromatography on silica gel (30% ethyl acetate/70% hexanes)
  10. customthen collected from hexanes

出典と根拠

ORDレコード
ord-eaa9d1d720194b459594019c4118fe86
出典データセット
uspto-grants-1998_03
特許番号
US05723410

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