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Penicillin G → 7-Aminocephalosporanic acid

HRID 638677
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HRID 638677 반응식
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10]C(CC3C=CC=CC=3)=O)[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([O-:22])=[O:21].[K+].CC1(C)S[C@@H]2[C@H](NC(COC3C=CC=CC=3)=O)C(=O)N2[C@H:27]1[C:45]([OH:47])=[O:46].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O.CC(OCC1CS[C@@H]2[C@H](NC(CCC[C@@H](N)C(O)=O)=O)C(=O)N2C=1C(O)=O)=O.O(CC(NC1C(=O)N2C(C(O)=O)=C(C)CS[C@H]12)=O)C1C=CC=CC=1.ClCC(NC1C(=O)N2C(C(O)=O)=C(C)CS[C@H]12)=O.C1(CC(NC2C(=O)N3C(C(O)=O)=C(C)CS[C@H]23)=O)C=CC=CC=1.C(NC1C(=O)N2C(C(O)=O)=C(C)CS[C@H]12)C1C=CC=CC=1>>[CH3:27][C:45]([O:47][CH2:23][C:2]1[CH2:1][S:6][C@@H:5]2[C@H:7]([NH2:10])[C:8](=[O:9])[N:4]2[C:3]=1[C:20]([OH:22])=[O:21])=[O:46]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

9

반응물 8

HCID 5904Penicillin GHCID 6869Penicillin VHCID 65536Cephalosporin CHCID 128952717-Phenylacetamido-3-methylceph-3-em-4-carboxylic acidHCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acidHCID 23664709Penicillin G Potassium
HCID 70444761
7-Chloracetamido-3-methylceph-3-em-4-carboxylic acid
HCID 704904127-Benzylamino-3-methylceph-3-em-4-carboxylic acid

생성물 1

HCID 4413287-Aminocephalosporanic acid

실험 절차

In an iminohalide/iminoether reaction for converting amido groups to amino groups present on a penicillin or cephalosporin selected from the group consisting of penicillin V, penicillin G, cephalosporin C, 6-chloracetamidopenicillanic acid, N-[2,2-diethoxycarbonylvinyl(1)]cephalosporin C, N-[2-nitro-2-carbethoxyvinyl(1)]cephalosporin C, 7-[N-(2,2-diethoxycarbonyl)vinyl]adipinoylamino-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acid, 7-[N-(2,2-diethoxycarbonyl)vinyl]adipinamido-3-[(2,5-dihydro-6-hydroxy-5-oxo-2-methyl-1,2,4-triazin-3-yl)thiomethyl]ceph-3-em-4-carboxylic acid, 7-[N-(2,2-diethoxycarbonyl)vinyl]adipinamido-3-[(4,5-dihydro-6-hydroxy-5-oxo-4-methyl-1,2,4-triazin-3-yl)thiomethyl]ceph-3-em-4-carboxylic acid, 3-desacetoxy-3-(1-methyl-1,2,3,4-tetrazol-5-yl)thiocephalosporin C, 3-desacetoxy-3-(2,5-dihydro-6-hydroxy-5-oxo-2-methyl-1,2,4-triazin-3-yl)thiocephalosporin C, 3-desacetoxy-3-(4,5-dihydro-6-hydroxy-5-oxo-4-methyl-1,2,4-triazin-3-yl)thiocephalosporin C, 7-phenoxyacetamido-3-methylceph-3-em-4-carboxylic acid, 7-chloracetamido-3-methylceph-3-em-4-carboxylic acid, 7-phenylacetamido-3-methylceph-3-em-4-carboxylic acid, N-ethoxycarbonylcephalosporin C, N-methoxycarbonylcephalosporin C, N-isobutoxycarbonylcephalosporin C, N-iso-propyloxycarbonylcephalosporin C, N-(N'-butylcarbamoyl)cephalosporin C, N-(N'-phenylcarbamoyl)cephalosporin C, N-chloracetylcephalosporin C, or 7-benzylamino-3-methylceph-3-em-4-carboxylic acid; to prepare an amino-compound of formula I, ##STR11## in which X is a group of formula II or IIa, ##STR12## in which R1 is methyl, methoxy, halogen, acetoxymethyl or --CH2 --S-heterocyclic, and esters and salts thereof,

출처 및 근거

ORD 기록
ord-517c699285bf463a850ca7823f7980ad
출처 데이터셋
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04562253

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