Pyridine → HCID 131713647, compound

HRID 358161Notes

Reaction equation

HRID 358161 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([CH:18]([O:25][C:26]([C:28]2[N:33]3[C:34](=[O:60])[C@@H:35]([NH:36][C:37](=[O:59])[C@@H:38]([C:52]4[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][CH:53]=4)[NH:39][C:40]([N:42]4[CH2:47][CH2:46][N:45]([CH2:48][CH3:49])[C:44](=[O:50])[C:43]4=[O:51])=[O:41])[C@H:32]3[S:31][CH2:30][C:29]=2[CH2:61][S:62][C:63]2[N:67]([CH3:68])[N:66]=[N:65][N:64]=2)=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:69]([C@:76](N)([C:82]([O:84][CH:85]([C:92]1[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=1)[C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)=[O:83])[CH2:77][O:78][C:79](Cl)=[O:80])([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70].[N:99]1C=CC=CC=1>O1CCCC1>[C:12]1([CH:18]([O:25][C:26]([C:28]2[N:33]3[C:34](=[O:60])[C@@H:35]([NH:36][C:37](=[O:59])[C@@H:38]([C:52]4[CH:53]=[CH:54][C:55]([N:58]([NH2:99])[C:79]([O:78][CH2:77][C@@H:76]([C:69]([O:71][C:72]([CH3:74])([CH3:73])[CH3:75])=[O:70])[C:82]([O:84][CH:85]([C:86]5[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=5)[C:92]5[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=5)=[O:83])=[O:80])=[CH:56][CH:57]=4)[NH:39][C:40]([N:42]4[CH2:47][CH2:46][N:45]([CH2:48][CH3:49])[C:44](=[O:50])[C:43]4=[O:51])=[O:41])[C@H:32]3[S:31][CH2:30][C:29]=2[CH2:61][S:62][C:63]2[N:67]([CH3:68])[N:66]=[N:65][N:64]=2)=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 88716346HCID 88716346, compoundHCID 88720460HCID 88720460, compound

Product 1

HCID 131713647HCID 131713647, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner described in Example 12, 3.2 g of 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7β-[(2R)-2-(4-aminophenyl)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester p-toluenesulphonate are reacted with 2.65 g of (2R)-2-BOC-amino-2-diphenylmethoxycarbonylethoxycarbonyl chloride and 0.67 ml of pyridine in 65 ml of tetrahydrofuran and worked up. The resulting crude product is chromatographed over 400 g of silica gel, and 500 ml fractions are taken. The fractions are eluted with toluene/ethyl acetate (1:1). By reprecipitating fractions 7-28 from CH2Cl2 /ether/hexane, 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7β-{(2R)-2-[4-((2R)-2-BOC-amino-2-diphenylmethoxycarbonylethoxycarbonylamino)-phenyl]-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido}-3-cephem-4-carboxylic acid diphenylmethyl ester is obtained. [α]D20 =-69°±1° (1.00% in CDCl3).

Workup

  1. customThe resulting crude product is chromatographed over 400 g of silica gel, and 500 ml fractions
  2. washThe fractions are eluted with toluene/ethyl acetate (1:1)
  3. customBy reprecipitating fractions 7-28 from CH2Cl2 /ether/hexane

Sources & evidence

ORD record
ord-dbf236e8c3204fce8d0ad98f20dd13d8
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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