Ethyl Acetate → HCID 178524880, 화합물

HRID 2169409노트

반응식

HRID 2169409 반응식
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])[N:9]=1)=[O:7])(C)(C)C.O[Li].O.C(OCC)(=O)C>O1CCCC1.O.CCCCCC>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450820HCID 178450820, 화합물

생성물 1

HCID 178524880HCID 178524880, 화합물수율 94.7%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (376) (14 g, 27.723 mmol) in tetrahydrofuran-water (15:7, 220 mL) was added LiOH.H2O (11.644 g, 277.228 mmol). The reaction mixture was refluxed for 16 h while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.1). After completion of the reaction, all volatiles were removed and the residue was diluted with water (50 mL) and neutralized to pH 7 with 1N HCl. The mixture was filtered and the resulting solid was dried to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (377) (11.8 g, 94.65%) as a white solid.

후처리

  1. temperatureThe reaction mixture was refluxed for 16 h while silica thin layer chromatography
  2. customAfter completion of the reaction
  3. customall volatiles were removed
  4. additionthe residue was diluted with water (50 mL)
  5. filtrationThe mixture was filtered
  6. customthe resulting solid was dried

출처 및 근거

ORD 기록
ord-56e78e9572824edbace6c0818f3c002e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

반응 노트

불러오는 중…