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2,6-Lutidine → 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(hydroxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid

HRID 1614917
ノート
印刷プレビュー

反応式

HRID 1614917 の反応式
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([CH2:23][CH2:24][P:25]([O:28]CC)([CH3:27])=[O:26])[C:14]([CH:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])[CH:6]=1.[Si](I)(C)(C)C.N1C(C)=CC=CC=1C>C(#N)C>[CH3:31][C:2]([CH3:1])([CH3:32])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([CH2:23][CH2:24][P:25]([OH:28])([CH3:27])=[O:26])[C:14]([CH:16]2[CH2:17][CH2:18][CH:19]([CH3:22])[CH2:20][CH2:21]2)=[O:15])[CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 85247Trimethylsilyl iodideHCID 670359145-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid

生成物 1

HCID 529173045-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(hydroxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid収率 36.3%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (108 mg, 0.225 mmol) was dissolved in acetonitrile (3 mL). This solution was cooled in an ice bath and TMSI (160 μL, 1.12 mmol) was added dropwise. The reaction turned yellow and some precipitate was formed. After approximately 1 minute 2,6-lutidine (156 μL, 1.35 mmol) was added, resulting in a clear solution. The ice bath was removed and the reaction was stirred at room temperature for 2 hours. Additional TMSI (50 μL) and 2,6-lutidine (50 μL) were added. After 45 minutes the reaction was determined by LC/MS to be complete. The reaction was cooled in an ice bath and additional 2,6-lutidine (100 μL) was added, followed by MeOH (2 mL). The reaction was warmed to room temperature and concentrated under vacuum. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(hydroxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (37 mg, 36%) was isolated from the residue by reverse phase HPLC. MS (m/z): 453.93 [M+H]+; 31P NMR (161.9 MHz, CD3OD): d 49.909.

後処理

  1. temperatureThis solution was cooled in an ice bath
  2. customsome precipitate was formed
  3. customresulting in a clear solution
  4. customThe ice bath was removed
  5. additionAdditional TMSI (50 μL) and 2,6-lutidine (50 μL) were added
  6. waitAfter 45 minutes the reaction was determined by LC/MS
  7. temperatureThe reaction was cooled in an ice bath
  8. additionadditional 2,6-lutidine (100 μL) was added
  9. temperatureThe reaction was warmed to room temperature
  10. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-f01d81f40cd04c93817e07b38ba35577
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765722B2

反応ノート

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