Acetic Acid → HCID 59643291, Verbindung

HRID 2251473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251473
[NH2:1][CH2:2][CH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1.[CH:18]([C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=2)[N:22]=1)([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH:18]([C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:27]=[CH:28][C:29]([CH2:30][NH:1][CH2:2][CH2:3][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:16][CH:17]=3)=[CH:32][CH:33]=2)[N:22]=1)([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 21320401Methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoateHCID 59643227HCID 59643227, Verbindung

Produkt 1

HCID 59643291HCID 59643291, VerbindungAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoate (1 g; 4.22 mmol) in dichloromethane (30 ml) was treated under nitrogen with 4-(5-isopropyl-1,2,4-oxadiazol-3-yl)benzaldehyde (0.96 g; 4.43 mmol), sodium triacetoxyborohydride (0.94 g; 4.43 mmol) and acetic acid (0.24 ml; 4.23 mmol). After stirring at rt overnight, the mixture was concentrated and partitioned between ethyl acetate and 1N NaOH. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography using an ethyl acetate-hexane gradient (20–70%) followed by a methanol-dichloromethane gradient (1–10%) afforded the title compound (1.5 g; 81% yield).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. custompartitioned between ethyl acetate and 1N NaOH
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-07e31dd665af4f2591b7f0a0893f73df
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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