Hydrochloric Acid → Methyl 3-amino-3-(4-butoxyphenyl)butanoate

HRID 1629799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629799
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:19]S(C(C)(C)C)=O)([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].Cl>CO>[NH2:19][C:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][CH:10]=1)([CH3:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86685892Methyl 3-(4-butoxyphenyl)-3-((tert-butylsulfinyl)amino)butanoate

Produkt 1

HCID 86685893Methyl 3-amino-3-(4-butoxyphenyl)butanoateAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of Intermediate 107B (1 g, 2.71 mmol) in MeOH (6 mL) was added 4 N HCl (3.38 mL, 13.53 mmol). The reaction was stirred at rt for 4 h. The reaction mixture was concentrated in vacuo and diluted with EtOAc. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to yield the desired product (700 mg, 97%) as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.38 (d, J=8.80 Hz, 2H), 6.86 (d, J=8.80 Hz, 2H), 3.95 (t, J=6.46 Hz, 2H), 3.59 (s, 3H), 1.73-1.80 (m, 2H), 1.53 (s, 2H), 1.45-1.52 (m, 2H), 1.19 (s, 3H), 0.98 (t, J=7.29 Hz, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2b81051b0a564aafba2f3fefd6f04a51
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791091B2

Notizen zur Reaktion

Wird geladen…