Sulfuric Acid → N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

HRID 1788826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788826
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([OH:14])[C:10](=[CH:12][CH:13]=1)[OH:11].[CH2:15]([O:22][C:23]([NH:25][CH:26](O)[C:27]([OH:29])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[CH2:15]([O:22][C:23]([N:25]([C:13]1[CH:12]=[C:10]([OH:11])[C:9]([OH:14])=[CH:8][C:7]=1[Cl:6])[CH2:26][C:27]([OH:29])=[O:28])=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 164964-ChlorocatecholHCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

Produkt 1

HCID 54341029N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Acetic acid (27 ml), concentrated sulphuric acid (3 ml) then 4-chlorocatechol (5.06 g. 35 mmole) were added to N-benzyloxycarbonyl 2-hydroxyglycine (6.75 g, 30 mmole) cooled in an ice bath. The mixture was stirred for one hour then poured onto ice and ethyl acetate and adjusted to pH7 with saturated sodium carbonate solution. The aqueous layer was collected, washed with ethyl acetate (100 ml), acidified to pH2 and extracted with ethyl acetate (3×75 ml). The extracts were washed with water (2×75 ml) and brine (50 ml) dried and evaporated to a gum which was crystallised from chloroform-cyclohexane, 5.90 g, 56%, mp 144°-145°, δ[(CD3)2CO] 5.06 (2H, s, OCH2), 5.64(1H, d, J8 Hz, CHNH), 6.6-7.0(1H, m, NH), 6.87 and 6.93(2H, 2×s, Ar), 7.30(5H, s, Ph) 8.0-9.4(3H, broad, 2×OH, CO2H). Found: C. 54.29; H, 4.04; Cl, 9.71; N, 4.07%. C16H14ClNO6 requires C, 54.63; H, 4.01; Cl, 10.08; N, 3.98%.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customThe aqueous layer was collected
  3. washwashed with ethyl acetate (100 ml)
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. washThe extracts were washed with water (2×75 ml) and brine (50 ml)
  6. customdried
  7. customevaporated to a gum which
  8. customwas crystallised from chloroform-cyclohexane, 5.90 g, 56%, mp 144°-145°, δ[(CD3)2CO] 5.06 (2H, s, OCH2), 5.64(1H

Quellen und Nachweise

ORD-Eintrag
ord-87ff1aaf786d4dafa35d8815afcd33ec
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04684639

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