Hydrochloric Acid → [(4-Hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)amino]-acetic acid methyl ester

HRID 722452

Reaktionsgleichung

Reaktionsgleichung von HRID 722452
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:26])[CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:26])[CH2:15][N:16]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl esterHCID 114240934-Hydroxybenzene-1-sulfonyl chloride

Produkt 1

HCID 67435286[(4-Hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)amino]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 8.7 g (45.2 mmol) of 4-hydroxybenzenesulfonyl chloride in 80 ml of CH2Cl2, a solution of 6.75 g (32.3 mmol) of (4-methoxy-benzylamino)-acetic acid methyl ester in 20 ml of CH2Cl2 and 12 ml (79.2 mmol) of triethylamine were added dropwise at 0° C. The resulting mixture is stirred for 4 h at r.t., neutralized with cold 1 N aqueous HCl and extracted with CH2Cl2. The combined extracts are washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; AcOEt:CH2Cl2=50:1˜5:1) to give [(4-hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)-amino]-acetic acid methyl ester; NMR (CDCl3): 3.57 (s, 3H), 3.79 (s, 3H), 3.90 (s, 2H), 4.40 (s, 2H), 5.59 (s, 1H), 6.84 (d, 2H, J=8.6 Hz), 6.93 (d, 2H, J=10.64 Hz), 7.15 (d, 2H, J=8.6 Hz), 7.82 (d, 2H, J=10.64 Hz).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts are washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel (eluent; AcOEt:CH2Cl2=50:1˜5:1)

Quellen und Nachweise

ORD-Eintrag
ord-707e94c687d34ed5b96fd3c94e407fc5
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138432B1

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