Triethylamine → 3-t-Butoxycarbonylaminomethyl-2-thienylacetic acid

HRID 26996

Reaktionsgleichung

Reaktionsgleichung von HRID 26996
[NH2:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C:9]([OH:11])=[O:10].C(N(CC)CC)C.[C:19]([O:23][C:24](N=[N+]=[N-])=[O:25])([CH3:22])([CH3:21])[CH3:20]>CC(C)=O>[C:19]([O:23][C:24]([NH:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C:9]([OH:11])=[O:10])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 159181433-Aminomethyl-2-thienylacetic acid

Produkt 1

HCID 159181443-t-Butoxycarbonylaminomethyl-2-thienylacetic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 3-aminomethyl-2-thienylacetic acid 8 (3.1 g, 18 m. moles) and triethylamine (8 g. 80 m moles) in 50% aqueous acetone (80 ml) was added dropwise t-butoxycarbonyl azide (5.7 g, 40 m moles) over a period of 20 mins. at 0° C. with vigorous stirring. The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. The concentrate was washed with ether (2×20 ml), adjusted to pH 2 with conc. HCl and extracted with ethyl acetate (2×50 ml). The ethyl acetate extracts were washed with saturated aqueous sodium chloride, dried over MgSO4, treated with charcoal and evaporated under reduced pressure. The residue was triturated with n-hexane and crystallized from n-hexane and benzene to give 4.5 g (92%) of colorless needles 9, melting at 62°-63° C.

Aufarbeitung

  1. customat 0° C.
  2. concentrationconcentrated under reduced pressure
  3. washThe concentrate was washed with ether (2×20 ml)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe ethyl acetate extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried over MgSO4
  7. additiontreated with charcoal
  8. customevaporated under reduced pressure
  9. customThe residue was triturated with n-hexane
  10. customcrystallized from n-hexane and benzene

Quellen und Nachweise

ORD-Eintrag
ord-0ebb8843cadb45a19a8b61f469ed62b0
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151352

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