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

HRID 571326노트

반응식

HRID 571326 반응식
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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 86681740methyl 2-(5,5-dimethyl-5'-(N-(2-morpholinoethyl)-methylsulfonamido)-2'-oxospiro[[1,3]dioxane-2,3'-indoline]-1'-yl)acetate

생성물 1

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

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

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온도
80 °C

실험 절차

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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-ac0f2e3ee7d04568840c391e2106b5d1
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024027B2

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