4-Methyloxybenzyl chloride → Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate

HRID 524402노트

반응식

HRID 524402 반응식
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[S:9][CH:10]=1)[CH3:2].C1CCN2C(=NCCC2)CC1.[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Cl)=[CH:35][CH:34]=1>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[N:7]=[C:8]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:37][C:36]2[CH:39]=[CH:40][C:33]([O:32][CH3:31])=[CH:34][CH:35]=2)[S:9][CH:10]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 699934-Methyloxybenzyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13240238ethyl (2-Boc-Aminothiazole-3-yl)acetate

생성물 1

HCID 67376904Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate수율 75.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2-tert-Butoxycarbonylamino-thiazol-4-yl)-acetic acid ethyl ester (7.5 g, 26.11 mmol) in 100 mL of dry dichloromethane was added DBU (11.96 g, 78.56 mmol) followed by para-methoxybenzyl chloride (6.15 g, 39.28 mmol) and the reaction mixture was stirred for 18 hrs at room temperature. The reaction was quenched with water and the layers were separated. The organic layer was washed with brine and dried over anhydrous sodium sulphate and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel 60-120 mesh and 2-10% ethyl acetate in hexanes as eluent) to get the pure compound (8.0 g).

후처리

  1. customThe reaction was quenched with water
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography (silica gel 60-120 mesh and 2-10% ethyl acetate in hexanes as eluent)

출처 및 근거

ORD 기록
ord-c3b29fac65f1409591996f72242bcd1e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340506B2

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