Hydrochloric Acid → 2-[3-(2-m-Tolyl-ethoxy)-4-trifluoromethyl-benzoylamino]-indane-2-carboxylic acid methyl ester

HRID 2094709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2094709
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([O:26][C:27](=O)[CH3:28])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:38][C:39]1[CH:40]=[C:41](CCO)[CH:42]=[CH:43][CH:44]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CO>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[C:18]([O:26][CH2:27][CH2:28][C:43]3[CH:44]=[C:39]([CH3:38])[CH:40]=[CH:41][CH:42]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 746483-MethylbenzeneethanolHCID 5363146Diisopropyl azodicarboxylateHCID 670766942-(3-Acetoxy-4-trifluoromethyl-benzoylamino)-indane-2-carboxylic acid methyl ester

Produkt 1

HCID 670766442-[3-(2-m-Tolyl-ethoxy)-4-trifluoromethyl-benzoylamino]-indane-2-carboxylic acid methyl esterAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

200 mg (0.48 mmol) of the compound of step 2 were dissolved in 5 ml of methanol, 13.1 mg (0.1 mmol) of potassium carbonate were added and the mixture was stirred for 30 min. The mixture was acidified with 1 N hydrochloric acid and extracted three times with 20 ml portions of EA. The combined organic phases were dried and evaporated. The residue was dissolved in 5 ml of THF, 96.9 mg (0.71 mmol) of 2-(3-methylphenyl)-ethanol and 186.7 mg (0.71 mmol) of triphenylphosphine were added, the mixture was cooled in an ice bath, and 191.9 mg (0.95 mmol) of DIAD were added. After stirring overnight, the mixture was evaporated to dryness and the residue was purified by preparative RP HPLC (water/ACN gradient). 104 mg of the title compound were obtained.

Aufarbeitung

  1. extractionextracted three times with 20 ml portions of EA
  2. customThe combined organic phases were dried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 5 ml of THF
  5. temperaturethe mixture was cooled in an ice bath
  6. stirringAfter stirring overnight
  7. customthe mixture was evaporated to dryness
  8. customthe residue was purified by preparative RP HPLC (water/ACN gradient)

Quellen und Nachweise

ORD-Eintrag
ord-a7c36e6208b54347b50cd9b3f469e68c
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445530B2

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