Water → Tafluprost

HRID 517398ノート

反応式

HRID 517398 の反応式
[F:1][C:2]([F:29])([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:3]=[CH:4]/[C@H:5]1[C@H:9]([OH:10])[CH2:8][C@H:7]([OH:11])[C@@H:6]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].C([O-])([O-])=O.[K+].[K+].I[CH:37]([CH3:39])[CH3:38].O>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]([F:29])([CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)/[CH:3]=[CH:4]/[C@H:5]1[C@H:9]([OH:10])[CH2:8][C@H:7]([OH:11])[C@@H:6]1[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:37]([CH3:39])[CH3:38])=[O:19]

参加物

7

反応物 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 9978917Tafluprost acid

生成物 1

HCID 9868491Tafluprost収率 105.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A solution of crude Tafluprost acid (12.0 g from Example 36) in DMF (100 mL) was treated with K2CO3 (21.1 g, 0.12 mol.) and 2-iodopropane (11.4 g, 0.08 mol.). This mixture was then stirred at 80° C. for 2 hr under an atmosphere of nitrogen (TLC monitoring). Water (100 mL) and ethyl acetate (100 mL) was added and the mixture was stirred for 10 min. The aqueous layer was separated and extracted with ethyl acetate (100 mL), the combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 14.0 g of crude Tafluprost. The crude Tafluprost was purified by column chromatography and then concentrated under reduced pressure to provide 6.8 g of Tafluprost (86% yield, 2 steps). HPLC (Phenomenex Luna 5 μm silica) analysis of the crude product showed that no isomer was detectable, and HPLC (Chiralcel OD-H) analysis of the crude product showed that no enantiomer was detectable.

後処理

  1. stirringthe mixture was stirred for 10 min
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (100 mL)
  4. dry with materialthe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a021b61958014e478aa974248c4a0ba5
出典データセット
uspto-grants-2015_08
特許番号
US09115109B2

反応ノート

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