Ethyl Acetate → HCID 178457452, 화합물

HRID 2169411노트

반응식

HRID 2169411 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Br:37])[N:15]=1)=[O:13])(C(C)(C)C)(C)C.C(OCC)(=O)C>O1CCCC1.Cl.CCCCCC>[OH:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Br:37])[N:15]=1)=[O:13]

참가 물질

6

반응물 2

HCID 8857Ethyl AcetateHCID 178457486HCID 178457486, 화합물

생성물 1

HCID 178457452HCID 178457452, 화합물수율 85.45%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (378) (5.7 g, 8.80 mmol) in tetrahydrofuran (50 mL), 1N HCl (15 mL) was added and the reaction mixture was stirred for 1 h at room temperature while silica thin layer chromatography was performed (70% ethyl acetate in hexane; Rf=0.2). After completion of the reaction, volatiles were removed and the residue was diluted with water (30 mL) and adjusted to pH 8 using NaHCO3. The aqueous mixture was extracted with ethyl acetate (2×150 mL) and the combined extracts were dried and concentrated. The resulting residue was purified by column over normal silica gel (100-200) to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylicacid(2-hydroxyethyl)-isopropylamide (379) (4.02 g, 85.45%) as a white solid.

후처리

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue was diluted with water (30 mL)
  4. extractionThe aqueous mixture was extracted with ethyl acetate (2×150 mL)
  5. customthe combined extracts were dried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column over normal silica gel (100-200)

출처 및 근거

ORD 기록
ord-446fdd30242542928f4fca99cb289326
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

반응 노트

불러오는 중…