Methyl iodide → 2-{2-[tert-Butoxycarbonyl-(4-methoxy-benzyl)-amino]-thiazol-4-yl}-propionic acid ethyl ester

HRID 524403노트

반응식

HRID 524403 반응식
[CH:1]([N-]C(C)C)(C)C.[Li+].[CH2:9]([O:11][C:12](=[O:36])[CH2:13][C:14]1[N:15]=[C:16]([N:19]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[S:17][CH:18]=1)[CH3:10].CI>C1COCC1>[CH2:9]([O:11][C:12](=[O:36])[CH:13]([C:14]1[N:15]=[C:16]([N:19]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[S:17][CH:18]=1)[CH3:1])[CH3:10]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 67376904Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate

생성물 1

HCID 673779002-{2-[tert-Butoxycarbonyl-(4-methoxy-benzyl)-amino]-thiazol-4-yl}-propionic acid ethyl ester수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of lithium diisopropylamide (prepared in situ) (4.24 g, 39.6 mmol) in dry THF (40 mL) was added the solution of {2-[tert-butoxycarbonyl-(4-methoxy-benzyl)-amino]-thiazol-4-yl}-acetic acid ethyl ester (8.0 g, 19.68 mmol) in 20 mL of dry THF in a dropwise fashion at −78° C. The reaction mixture was continued to stir at −78° C. for 1 hour followed by the addition of methyl iodide (4.19 g, 29.52 mmol) at the same temperature. The reaction mixture was kept on stirring and slowly allowed to come to room temperature. The reaction mixture was quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine and dried over anhydrous sodium sulphate and the solvent was removed in vacuo to get the sticky compound (8.2 g). The compound was used for the next reaction without any purification.

후처리

  1. stirringon stirring
  2. customto come to room temperature
  3. customThe reaction mixture was quenched with saturated ammonium chloride solution
  4. additiondiluted with ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-d1f03dd36f364adf84e60ebd681feb0d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340506B2

반응 노트

불러오는 중…