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

HRID 923547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923547
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

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-360bc8f414504df4b93b52649843abbc
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278910B2

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