Sulfuric Acid → HCID 67153982, compound
Reaction equation
[F:1][CH:2]([F:28])[CH2:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:27])/[CH:24]=N/O)=[CH:18][CH:17]=1)([CH2:11][CH2:12][CH:13]([F:15])[F:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7].S(=O)(=O)(O)[OH:30]>>[F:14][CH:13]([F:15])[CH2:12][CH2:11][C:5]([C:16]1[CH:17]=[C:18]2[C:19](=[CH:20][CH:21]=1)[NH:22][C:23](=[O:27])[C:24]2=[O:30])([CH2:4][CH2:3][CH:2]([F:1])[F:28])[C:6]([O:8][CH2:9][CH3:10])=[O:7]Participants
Conditions
- Temperature
- 50 °C
Procedure
3.0 g of ethyl 2-(3,3-difluoropropyl)-5,5-difluoro-2-[4-[[(2E)-2-hydroxyiminoacetyl]amino]phenyl]pentanoate are added in portions to 20 ml of sulfuric acid (98%) at 50° C., during which the temperature rises to 60° C. When the addition is complete, the mixture is stirred at 50° C. for a further 120 min and subsequently poured into 400 ml of ice-water. The mixture is washed three times with 200 ml of dichloromethane/ethanol (9:1) each time, the combined organic phases are dried over sodium sulfate, filtered off and evaporated to dryness in vacuo. The crude product obtained is employed in the next reaction without further purification. Yield: 1.9 g (66%) of ethyl 2-(3,3-difluoropropyl)-2-(2,3-dioxoindolin-5-yl)-5,5-difluoropentanoate obtained; LC-MS retention time: 2.17 min.
Workup
- customrises to 60° C
- additionWhen the addition
- washThe mixture is washed three times with 200 ml of dichloromethane/ethanol (9:1) each time
- dry with materialthe combined organic phases are dried over sodium sulfate
- filtrationfiltered off
- customevaporated to dryness in vacuo
- customThe crude product obtained
- customis employed in the next reaction without further purification
Sources & evidence
- ORD record
- ord-476a7864903446429cd1ec36461cae4a
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906930B2
Reaction notes
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