[4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acid → Tert-butyl(+/-)-3-(3-{[{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)-acetyl]amino}-2-methylphenyl)propanoate

HRID 877189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877189
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:13]([OH:15])=O)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[NH2:21][C:22]1[C:23]([CH3:37])=[C:24]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:25]=[CH:26][CH:27]=1>CN(C=O)C.N1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:13]([NH:21][C:22]2[C:23]([CH3:37])=[C:24]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH:25]=[CH:26][CH:27]=2)=[O:15])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 58136423[4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acidHCID 58136633Tert-butyl 3-(3-amino-2-methylphenyl)propanoate

Produkt 1

HCID 58136347Tert-butyl(+/-)-3-(3-{[{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)-acetyl]amino}-2-methylphenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

11.41 g (90% pure, 37.16 mmol) of (+/−)-{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)acetic acid were dissolved in a mixture of 71.8 ml of DMF and 22.5 ml of pyridine, and 15.54 g (40.88 mmol) of 1-[bis(dimethylamino)methylene]-5-chloro-3-oxy-1H-benzotriazol-1-ium tetrafluoroborate and 8.75 g (37.16 mmol) of tert-butyl 3-(3-amino-2-methylphenyl)propanoate were added. The reaction mixture was stirred at RT overnight and then concentrated under high vacuum. The residue was taken up in 100 ml of ethyl acetate and washed successively with 10% strength aqueous citric acid, saturated sodium bisulfate solution and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→3:1). This gave 16.36 g (89.2% of theory) of the title compound.

Aufarbeitung

  1. additionwere added
  2. concentrationconcentrated under high vacuum
  3. washwashed successively with 10% strength aqueous citric acid, saturated sodium bisulfate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→3:1)

Quellen und Nachweise

ORD-Eintrag
ord-7a277a690a884f58a97018958aabb3ac
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987256B2

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