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

HRID 492739ノート

反応式

HRID 492739 の反応式
[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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-39687eda882b47ec8d8fd89b425a8429
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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