Methyl iodide → Bimatoprost acid methyl ester

HRID 517408ノート

反応式

HRID 517408 の反応式
[OH:1][C@@H:2]1[CH2:6][C@H:5]([OH:7])[C@H:4]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C@H:3]1/[CH:17]=[CH:18]/[C@@H:19]([OH:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:29](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[OH:1][C@@H:2]1[CH2:6][C@H:5]([OH:7])[C@H:4]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:29])=[O:15])[C@H:3]1/[CH:17]=[CH:18]/[C@@H:19]([OH:28])[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5283081Bimatoprost Acid

生成物 1

HCID 29935774Bimatoprost acid methyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

A solution of (5Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopentyl)hept-5-enoic acid (2 g from Example 53) was dissolved in 20 ml N,N-dimethylformamide in 50 mL round-bottom flask, followed by addition of potassium carbonate (2.2 g, 16.2 mmol) and iodomethane (1.1 g, 8.1 mmol). The reaction mixture was heated to 40° C. and stirred for 2 hours. The mixture was cooled to room temperature and the solid was filtered off. The filtrate was subsequently diluted and extracted with 20 ml ethyl acetate and 20 ml water. The mixture was phase separated and the organic layer was dried over anhydrous MgSO4, the solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield of the title compound was 1.6 g (73.5% in 2 steps)

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe solid was filtered off
  3. additionThe filtrate was subsequently diluted
  4. extractionextracted with 20 ml ethyl acetate and 20 ml water
  5. customseparated
  6. dry with materialthe organic layer was dried over anhydrous MgSO4
  7. filtrationthe solid was filtered off
  8. customorganic solvent was evaporated off under vacuum
  9. customThe crude product was purified by chromatography on silica gel using
  10. additiona mixture of hexane and ethyl acetate as a gradient eluent

出典と根拠

ORDレコード
ord-8b652eda24664b7d840e9d64d55c1c87
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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