Isoamyl Nitrite → Boc-Leu-DTrp-betaAla-OEt

HRID 129987ノート

反応式

HRID 129987 の反応式
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23]N)=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.O1CCOCC1.N(OCCC(C)C)=O.N[CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51].Cl>CN(C=O)C>[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

参加物

6

反応物 4

HCID 8053Isoamyl NitriteHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 11070055Boc-Leu-DTrp-NHNH2HCID 204431481,4-Dioxane hydrochloride

生成物 1

HCID 131719104Boc-Leu-DTrp-betaAla-OEt収率 87.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-20 °C

実験手順

To a solution of Boc-Leu-DTrp-NHNH2 (39 mg) obtained in Example 1-(2) in DMF (0.5 ml) was added 3.1 M HCl/1,4-dioxane (81 μl) at -60° C. The temperature of the solution was raised to -20° C. and isoamyl nitrite (15 μl) was added. The reaction mixture was stirred at -20° C. to -15° C. for 1.5 h and cooled at -60° C. A solution of βAla-OEt.HCl (17 mg) in DMF (0.5 ml) and TEA (50 μl) were added. The reaction mixture was stirred at 5° C. overnight and concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development to give the product (41 mg).

後処理

  1. temperaturecooled at -60° C
  2. stirringThe reaction mixture was stirred at 5° C. overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between water and dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development

出典と根拠

ORDレコード
ord-3462bd9829aa4cf08735b6938a2e38f1
出典データセット
uspto-grants-1995_11
特許番号
US05470833

反応ノート

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