Hydrochloric Acid → 4-(4-Benzyloxycarbonylamino-3-fluorophenyl)pyridine-2-carboxylic acid

HRID 492739노트

반응식

HRID 492739 반응식
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]([O:26]C)=[O:25])[CH:19]=2)=[CH:14][C:13]=1[F:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[OH-].[Li+].Cl>C(O)C.CO.CN(C)C=O.CCCCCC.C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]([OH:26])=[O:25])[CH:19]=2)=[CH:14][C:13]=1[F:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

10

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 23153492Methyl 4-(4-benzyloxycarbonylamino-3-fluorophenyl)pyridine-2-carboxylate

생성물 1

HCID 231533734-(4-Benzyloxycarbonylamino-3-fluorophenyl)pyridine-2-carboxylic acid수율 86.1%

시약·촉매·용매 5

HCID 702Ethanol용매HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 8058Hexane용매

실험 절차

Methyl 4-(4-benzyloxycarbonylamino-3-fluorophenyl)pyridine-2-carboxylate (1.02 g) was dissolved in a mixed solvent of ethanol (25 ml), methanol (50 ml) and N,N-dimethylformamide (7.5 ml), and then water (7.5 ml) was added. Lithium hydroxide monohydrate (185 mg) was added thereto at room temperature while stirring, followed by stirring at room temperature for 1.5 hrs. To the reaction mixture was added 1 N HCl (30 ml), followed by concentrating under a reduced pressure. To the resultant residue was added a mixed solvent of ethyl acetate (100 ml) and tetrahydrofuran (100 ml) to partition. The organic layer was washed with brine (50 ml×3), and dried over anhydrous sodium sulfate. The solvent was evaporated to give a solid, which was then suspended in a mixed solvent of diethyl ether (20 ml) and hexane (20 ml), filtered, and dried under aeration to provide the titled compound (846 mg, 86.1%) as a pale brown solid.

후처리

  1. stirringby stirring at room temperature for 1.5 hrs
  2. concentrationby concentrating under a reduced pressure
  3. additionTo the resultant residue was added a mixed solvent of ethyl acetate (100 ml) and tetrahydrofuran (100 ml)
  4. customto partition
  5. washThe organic layer was washed with brine (50 ml×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customto give a solid, which
  9. filtrationfiltered
  10. customdried under aeration

출처 및 근거

ORD 기록
ord-39687eda882b47ec8d8fd89b425a8429
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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