Ammonium Chloride → 4-Fluoro-2-[1-(4-methoxy-benzyl)-1h-benzotriazol-4-yloxy]-benzoic acid methyl ester

HRID 1848905노트

반응식

HRID 1848905 반응식
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=3[N:10]=[N:9]2)=[CH:5][CH:4]=1.F[C:21]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].CC(C)([O-])C.[K+].[Cl-].[NH4+]>COCCOCCOC>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:30][C:29]([F:31])=[CH:28][C:27]=1[O:17][C:16]1[C:11]2[N:10]=[N:9][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2782897Methyl 2,4-DifluorobenzoateHCID 23665647Potassium tert-butoxideHCID 1363439141-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

생성물 1

HCID 672269974-Fluoro-2-[1-(4-methoxy-benzyl)-1h-benzotriazol-4-yloxy]-benzoic acid methyl ester

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
100 °C

실험 절차

To a solution of EXAMPLE 342C (990 mg) and methyl 2,4-difluorobenzoate (734 mg) in diglyme (40 mL) was added potassium tert-butoxide (1M in tetrahydrofuran, 4.07 mL). The solution was heated to 100° C. for 16 hours, cooled, added to saturated ammonium chloride, and extracted with 70% ethyl acetate in hexanes. The extract was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography on silica gel using 30% ethyl acetate in hexanes.

후처리

  1. temperaturecooled
  2. extractionextracted with 70% ethyl acetate in hexanes
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel using 30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-a658098a6c444399ad413f9f6826a61c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952157B2

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