Hydrochloric Acid → 6-Acetyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-indole

HRID 381340ノート

反応式

HRID 381340 の反応式
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:19]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[O:21])=[CH:14][N:15]2[CH3:18])=[CH:11][CH:10]=1)=[O:8].Cl>C(OCC)C.O1CCCC1>[C:7]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:19]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:20]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)(=[O:24])=[O:25])=[O:21])=[CH:14][N:15]2[CH3:18])=[CH:11][CH:10]=1)(=[O:8])[CH3:1]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 22467206N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 224672486-Acetyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-indole

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

Methylmagnesium bromide (0.23 ml of a 3M solution in diethyl ether) was added dropwise to a stirred solution of N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamide (from Example 103, 174 mg, 0.32 mmol) in anhydrous tetrahydrofuran (5 ml) at −70° C. under a nitrogen atmosphere. The mixture was stirred at −70° C. for an additional 2 hours before warming to room temperature. Aqueous hydrochloric acid (5 ml of 1M solution) was slowly added to the mixture, and then it was extracted with ethyl acetate (100 ml). The organic phase was separated and washed with brine, dried (magnesium sulphate) and the solvent were removed in vacuo. The residue was flash chromatographed using a gradient elution of a mixture of 90% hexane and 10% ethyl acetate, through to 100% ethyl acetate, to give the title compound (18 mg).

後処理

  1. temperaturebefore warming to room temperature
  2. extractionit was extracted with ethyl acetate (100 ml)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent were removed in vacuo
  7. customchromatographed
  8. washa gradient elution of a mixture of 90% hexane and 10% ethyl acetate

出典と根拠

ORDレコード
ord-401b87f3e53e4825aacbaa624cbdcd61
出典データセット
uspto-grants-2001_10
特許番号
US06306852B1

反応ノート

読み込み中…