Hydrochloric Acid → HCID 86739992、化合物

HRID 2164664ノート

反応式

HRID 2164664 の反応式
[CH2-]C(C)=O.[C:5]1([CH3:20])[CH:10]=[CH:9][C:8]([S:11]([O:14][CH2:15][CH:16]([OH:19])CO)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[Br:21][CH:22]1[CH2:30][CH2:29][C:28]2[N:27]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[CH:26]=[CH:25][C:24]=2[C:23]1=[O:41].Cl.[OH-].[Na+]>O.C1C=CC=CC=1>[C:5]1([CH3:20])[CH:6]=[CH:7][C:8]([S:11]([O:14][CH:15]2[CH2:16][O:19][C:23]3([CH:22]([Br:21])[CH2:30][CH2:29][C:28]4[N:27]([S:31]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)(=[O:33])=[O:32])[CH:26]=[CH:25][C:24]3=4)[O:41]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 129463865-Bromo-1-(4-methylbenzene-1-sulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-oneHCID 178427781HCID 178427781、化合物

生成物 1

HCID 86739992HCID 86739992、化合物収率 42%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

A mixture of 3-p-toluenesulfonyloxypropyleneglycol acetonide (2 molar equivalents), 5-bromo-1-p-toluenesulfonyl-4-oxo-4,5,6,7-tetrahydroindole (100 parts), hydrochloric acid (1 molar equivalent) and benzene (500 to 2000 parts) is refluxed for 21 hours under azeotropic dehydration. After cooling, the reaction mixture is adjusted to pH 10 with 5N-sodium hydroxide, shaken and water layer drained. Organic layer is washed with water, (100 parts) and dried over anhydrous sodium sulfate (50 parts). The drying agent is removed by filtration. The filtrate is then concentrated under reduced pressure at a temperature below 50° C. to leave amorphous 4'-p-toluenesulfonyloxy-1-p-toluenesulfonyl-5-bromo-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]-dioxolane diastereomer mixture in 42% yield. The product is shown in Table I, Part 6, No. 18.

後処理

  1. temperatureis refluxed for 21 hours under azeotropic dehydration
  2. temperatureAfter cooling
  3. washOrganic layer is washed with water, (100 parts)
  4. dry with materialdried over anhydrous sodium sulfate (50 parts)
  5. customThe drying agent is removed by filtration
  6. concentrationThe filtrate is then concentrated under reduced pressure at a temperature below 50° C.

出典と根拠

ORDレコード
ord-69976aea8fd041daae81bd7dcc4809c9
出典データセット
uspto-grants-1985_03
特許番号
US04506079

反応ノート

読み込み中…