Pyridine → HCID 131713653, compound

HRID 358168Notes

Reaction equation

HRID 358168 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][O:62][C:63](=[O:65])[CH3:64])=[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:66]([C@:73](N)([C:79]([O:81][CH:82]([C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1)[C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1)=[O:80])[CH2:74][O:75][C:76](Cl)=[O:77])([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67].[N:96]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:57]=[CH:56][C:55]([N:58]([NH2:96])[C:76]([O:75][CH2:74][C@@H:73]([C:66]([O:68][C:69]([CH3:71])([CH3:70])[CH3:72])=[O:67])[C:79]([O:81][CH:82]([C:83]5[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=5)[C:89]5[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=5)=[O:80])=[O:77])=[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][O:62][C:63](=[O:65])[CH3:64])=[O:27])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 88716346HCID 88716346, compoundHCID 88719411HCID 88719411, compound

Product 1

HCID 131713653HCID 131713653, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner described in Example 12, 4.56 g of 3-acetoxymethyl-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 3.8 g of (2R)-2-BOC-amino-2-diphenylmethoxycarbonylethoxycarbonyl chloride and 0.95 ml of pyridine in 135 ml of tetrahydrofuran and worked up. Th resulting crude product is chromatographed over 400 g of silica gel (500 ml fractions), fractions 1-12 being eluted with toluene/ethyl acetate (3:2) and the later fractions with toluene/ethyl acetate (1:1). By reprecipitating fractions 9-23 from CH2Cl2 /ether/hexane, 3-acetoxymethyl-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 =+8°±1° (0.82% in CHCl3).

Workup

  1. customTh resulting crude product is chromatographed over 400 g of silica gel (500 ml fractions), fractions 1-12
  2. washbeing eluted with toluene/ethyl acetate (3:2)
  3. customBy reprecipitating fractions 9-23 from CH2Cl2 /ether/hexane

Sources & evidence

ORD record
ord-f626c18559f6402789adcf8b749181d5
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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