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

反応式

HRID 4110 の反応式
[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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddaa86d81d414c41b26b1fb192d4a590
出典データセット
uspto-grants-1988_02
特許番号
US04723002

関連ノート

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