Water → (+/-)-tert-Butyl 3-{3-[(cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-acetyl)amino]-2-methylphenyl}propanoate

HRID 877227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877227
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:10]([NH:12][C:13]2[C:14]([CH3:28])=[C:15]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH:34]1[CH:39]=[C:38]([CH:40]=[O:41])[C:37]([CH:42]=O)=[CH:36][CH:35]=1.O>C(O)(=O)C>[CH:29]1([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:1]3[CH2:42][C:37]4[C:38](=[CH:39][CH:34]=[CH:35][CH:36]=4)[C:40]3=[O:41])=[CH:4][CH:5]=2)[C:10]([NH:12][C:13]2[C:14]([CH3:28])=[C:15]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:30][CH2:31][CH2:32][CH2:33]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4807PhthalaldehydeHCID 58136676(+/-)-Tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Produkt 1

HCID 58136664(+/-)-tert-Butyl 3-{3-[(cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-acetyl)amino]-2-methylphenyl}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

At RT, 50 mg (0.11 mmol) of (+/−)-tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate and 16.4 mg (0.12 mmol) of phthaldialdehyde were dissolved in 2.5 ml of glacial acetic acid, and the mixture was left to stand for 1 h. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by preparative RP-HPLC. This gave 53 mg (85% of theory) of the target compound.

Aufarbeitung

  1. waitthe mixture was left
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ecd2656d1d5c4c2d9aaa8a390acf87ba
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987256B2

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