Tetrahydrofuran → 6-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid

HRID 340435ノート

反応式

HRID 340435 の反応式
[OH-].[Na+].O1CCCC1.[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([Cl:34])[N:24]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CO>[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([Cl:34])[N:24]=1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86683846Methyl 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinate

生成物 1

HCID 866838426-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid収率 103.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

A 1N sodium hydroxide aqueous solution (15 ml) was added to a solution of tetrahydrofuran (30 ml) and methanol (30 ml) containing methyl 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinate (3.00 g), followed by stirring at 65° C. for 2 hours. The reaction mixture was cooled to room temperature, the solvent was distilled away under reduced pressure, and a saturated aqueous ammonium chloride solution, tetrahydrofuran, and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Colorless oily matter of 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid (3.00 g) was thus obtained.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled away under reduced pressure
  3. additiona saturated aqueous ammonium chloride solution, tetrahydrofuran, and ethyl acetate were added
  4. customThe organic layer was collected
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure

出典と根拠

ORDレコード
ord-9744dc2a55a84b74b835032aea51879e
出典データセット
uspto-grants-2014_11
特許番号
US08895585B2

反応ノート

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