Methyl iodide → N-methyl-N-6-bromohexanoyl-L-leucine ethyl ester

HRID 864467노트

반응식

HRID 864467 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:21])[C@H:7]([CH2:17][CH:18]([CH3:20])[CH3:19])[NH:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH3:4].[CH3:22]I>C1COCC1>[CH2:3]([O:5][C:6](=[O:21])[C@H:7]([CH2:17][CH:18]([CH3:20])[CH3:19])[N:8]([CH3:22])[C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH3:4]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22866411N-6-bromohexanoyl-L-leucine ethyl ester

생성물 1

HCID 22866412N-methyl-N-6-bromohexanoyl-L-leucine ethyl ester수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60% dispersion in oil; 2.0 g, 50 mmol) was added to a stirred solution of N-6-bromohexanoyl-L-leucine ethyl ester (15.0 g, 45 mmol) in anhydrous THF (150 ml) at 0° C. After the effervesence had ceased methyl iodide (8.4 ml) was added. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate, washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated to give crude N-methyl-N-6-bromohexanoyl-L-leucine ethyl ester (14.0 g, 89%) as a pale yellow oil which was used directly in the next step.

후처리

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b3639f26501d4ed28d8a2c71019678fb
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563151

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