Trifluoroacetic acid → 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-2,3-dioxoindolin-1-yl)acetic acid 2,2,2-trifluoroacetic acid salt

HRID 571326ノート

反応式

HRID 571326 の反応式
CC1(C)CO[C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N:14]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=3)[N:7]([CH2:27][C:28]([O:30]C)=[O:29])[C:6]2=[O:32])[O:4]C1.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(OCC)(=O)C.CCCCCC>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[O:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][N:14]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:27][C:28]([OH:30])=[O:29])[C:6](=[O:32])[C:5]3=[O:4])[S:15]([CH3:18])(=[O:17])=[O:16])[CH2:22][CH2:23]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 86681740methyl 2-(5,5-dimethyl-5'-(N-(2-morpholinoethyl)-methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

生成物 1

HCID 866817412-(5-(N-(2-morpholinoethyl)methylsulfonamido)-2,3-dioxoindolin-1-yl)acetic acid 2,2,2-trifluoroacetic acid salt収率 69%

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 2-(5,5-dimethyl-5′-(N-(2-morpholinoethyl)-methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (0.450 g, 0.880 mmol) and TFA (0.678 ml, 8.80 mmol) in dioxane/water 1/1 (15 ml) was heated at 80° C. for 24 hours. Additional TFA (1.356 ml, 17.6 mmol) was added over 5 days with stirring at the same temperature. The volatiles were removed under vacuum, and the crude was triturated with diethyl ether. The insoluble was collected by filtration and dried under vacuum affording 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-2,3-dioxoindolin-1-yl)acetic acid 2,2,2-trifluoroacetic acid salt (0.319 g, 0.607 mmol, 69.0% yield, MS/ESI+ 412.0 [MH]+).

後処理

  1. customThe volatiles were removed under vacuum
  2. customthe crude was triturated with diethyl ether
  3. filtrationThe insoluble was collected by filtration
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-ac0f2e3ee7d04568840c391e2106b5d1
出典データセット
uspto-grants-2015_05
特許番号
US09024027B2

反応ノート

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