Acetic Acid → tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate

HRID 923547노트

반응식

HRID 923547 반응식
C(OC1C=CC(C([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH2:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C:24](=[O:47])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:46])[CH2:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[C:42]([F:45])([F:44])[F:43])=[CH:27][CH:26]=3)=[CH:18][CH:17]=2)=O)=CC=1)CCCCCC.CO.[OH-].[Na+].CC(O)=O>C1COCC1>[OH:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:48][C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])[C:24](=[O:47])[C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:46])[CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=3[C:42]([F:44])([F:45])[F:43])=[CH:29][CH:30]=2)=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 892850004-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate

생성물 1

HCID 71076732tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Prepared using General Procedure 9: To a stirring solution of 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-6 (2.53 g, 3.20 mmol) in THF (10 mL) and MeOH (50 mL) was added 2N NaOH (3.2 mL). The reaction mixture was stirred at room temperature for 10 min. The reaction mixture was acidified with AcOH. The crude mixture was concentrated then diluted with DCM (150 mL) and washed with brine (200 mL). The organic layer was concentrated and purified by chromatography (EA/hexanes) to afford 1.64 g (88%) of tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate INT-9. LCMS-ESI (m/z) calculated for C30H31F3N2O6: 572; found 571 [M−H]−, tR=2.30 min. (Method 3).

후처리

  1. customPrepared
  2. concentrationThe crude mixture was concentrated
  3. additionthen diluted with DCM (150 mL)
  4. washwashed with brine (200 mL)
  5. concentrationThe organic layer was concentrated
  6. custompurified by chromatography (EA/hexanes)

출처 및 근거

ORD 기록
ord-360bc8f414504df4b93b52649843abbc
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278910B2

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