Ampicillin → Benzyloxy (ethyloxy)phosphinyl isocyanate

HRID 267998

反応式

HRID 267998 の反応式
C(O[N-:9][PH:10]([O:12][CH2:13][CH3:14])=[O:11])C1C=CC=CC=1.[C:15](Cl)(Cl)=[O:16].[N-]=C=[O:21].CC1(C)S[C@@H]2[C@H](NC([C@H:34](N)[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=O)C(=O)N2[C@H]1C(O)=O.CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C([O-])=O.[K+].[Na]>ClCCl.C1(C)C=CC=CC=1.O.N1C=CC=CC=1>[CH2:34]([O:11][P:10]([N:9]=[C:15]=[O:16])([O:12][CH2:13][CH3:14])=[O:21])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

11

反応物 6

HCID 6249Ampicillin2 回HCID 6371PhosgeneHCID 105034Isocyanate2 回HCID 5360545SodiumHCID 23664709Penicillin G PotassiumHCID 178476827HCID 178476827、化合物

生成物 1

HCID 20384063Benzyloxy (ethyloxy)phosphinyl isocyanate

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of crude benzyloxy (ethyloxy)phosphinyl isocyanate [(C6H5CH2O) (C2H5O)P(O)-NCO] in 30 ml of dry dichloromethane was prepared by reaction of 30 mmol of crude benzyloxy(ethoxy) phosphinylamide [(C6H5CH2O) (C2H5 0)P(O)--NH2 ] with phosgene in toluene in the presence of pyridine followed by in vacuo removal of solvents. According to an IR spectrum, the solution contained approximately 20 mmol of the isocyanate. In the mean time, a solution was prepared in the usual manner starting from 7.0 g (20 mmol) of D(-) ampicillin, 5.0 ml of BSA and 30 ml of dichloromethane. This solution was cooled down to 0°C whereupon the solution of the isocyanate was added in 5 minutes and according to thin-layer chromatograms, ampicillin was about two thirds converted into the desired penicillin. The reaction mixture was poured in iced water of pH 7.0, followed by in vacuo removal of dichloromethane. Ethyl acetate was added and the pH lowered to 3.5. The layers were separated and extraction was continued until the greatest part of the penicillin was extracted. The combined extracts were washed with iced water, dried over anhydrous magnesium sulfate, concentrated in vacuo to small volume whereupon sodium α-ethylcapronate was added, etc to obtain 8.0 g (62%) of the above named sodium salt in good state of purity.

後処理

  1. customfollowed by in vacuo removal of solvents
  2. customIn the mean time, a solution was prepared in the usual manner
  3. additionwas added in 5 minutes
  4. customfollowed by in vacuo removal of dichloromethane
  5. additionEthyl acetate was added
  6. customThe layers were separated
  7. extractionextraction
  8. extractionwas extracted
  9. washThe combined extracts were washed with iced water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo to small volume whereupon sodium α-ethylcapronate
  12. additionwas added
  13. custometc to obtain 8.0 g (62%) of the

出典と根拠

ORDレコード
ord-f759e12b51c94cd484dcdffb329cb362
出典データセット
uspto-grants-1976_03
特許番号
US03945994

関連ノート

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