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

HRID 923547ノート

反応式

HRID 923547 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-360bc8f414504df4b93b52649843abbc
出典データセット
uspto-grants-2016_03
特許番号
US09278910B2

反応ノート

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