Trifluoroacetic acid → (2S-trans)-3-Amino-2-methyl-4-oxo-1-azetidinephosphonic acid, 2-(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-2-oxoethyl ester, trifluoroacetate salt

HRID 4110

Reaktionsgleichung

Reaktionsgleichung von HRID 4110
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1[C:10](=[O:36])[CH:11]=[C:12]([C:15](=[O:35])[CH2:16][O:17][P:18]([OH:34])([N:20]2[C:23](=[O:24])[C@@H:22]([NH:25]C(=O)OC(C)(C)C)[C@@H:21]2[CH3:33])=[O:19])[NH:13][CH:14]=1.[K].C1(OC)C=CC=CC=1>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:25][C@@H:22]1[C:23](=[O:24])[N:20]([P:18]([O:17][CH2:16][C:15]([C:12]2[NH:13][CH:14]=[C:9]([OH:8])[C:10](=[O:36])[CH:11]=2)=[O:35])(=[O:19])[OH:34])[C@H:21]1[CH3:33]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 5462222PotassiumHCID 131715443(2S-trans)-[1-[[2-(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, 1,1-dimethylethyl ester

Produkt 1

HCID 131715441(2S-trans)-3-Amino-2-methyl-4-oxo-1-azetidinephosphonic acid, 2-(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-2-oxoethyl ester, trifluoroacetate salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (3 ml) was added to a 5° C. stirred suspension of (2S-trans)-[1-[[2-(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, 1,1-dimethylethyl ester, monopotassium salt (375 mg) in 4 ml of dry dichloromethane containing 1 ml of anisole. After about three minutes, the solid dissolved and the mixture was stirred for 1.25 hours at 5° C. TLC indicated the reaction was essentially complete. Toluene (2 ml) was added and the mixture was concentrated in vacuo to a viscous brown oil. The oil was washed twice with hexane, then triturated with ether. The resultant solid was washed twice with ether and dried in vacuo to afford 0.437 g of crude title compound, which was used directly in the next step.

Aufarbeitung

  1. dissolutionthe solid dissolved
  2. stirringthe mixture was stirred for 1.25 hours at 5° C
  3. concentrationthe mixture was concentrated in vacuo to a viscous brown oil
  4. washThe oil was washed twice with hexane
  5. customtriturated with ether
  6. washThe resultant solid was washed twice with ether
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ddaa86d81d414c41b26b1fb192d4a590
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723002

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