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

Reaction equation

HRID 4110 reaction equation
[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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ddaa86d81d414c41b26b1fb192d4a590
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Linked notes

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