Ampicillin → Benzyloxy (ethyloxy)phosphinyl isocyanate

HRID 267998

반응식

HRID 267998 반응식
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

참가 물질

11

반응물 6

HCID 6249Ampicillin2회HCID 6371PhosgeneHCID 105034Isocyanate2회HCID 5360545SodiumHCID 23664709Penicillin G PotassiumHCID 178476827HCID 178476827, 화합물

생성물 1

HCID 20384063Benzyloxy (ethyloxy)phosphinyl isocyanate

시약·촉매·용매 4

HCID 962Water용매HCID 1049Pyridine용매HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f759e12b51c94cd484dcdffb329cb362
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03945994

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