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

HRID 129987노트

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HRID 129987 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 131719104Boc-Leu-DTrp-betaAla-OEt수율 87.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
-20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3462bd9829aa4cf08735b6938a2e38f1
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470833

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