Pyridine → HCID 131713654, compound

HRID 358169Notes

Reaction equation

HRID 358169 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 88721266HCID 88721266, compound

Product 1

HCID 131713654HCID 131713654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner described in Example 12, 3.63 g of 3-acetoxymethyl-7β-[(2S)-2-(4-aminophenyl)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester p-toluenesulphonate are reacted with 3.03 g of (2R)-2-BOC-amino-2-diphenylmethoxycarbonylethoxycarbonyl chloride and 0.76 ml of pyridine in 100 ml of tetrahydrofuran and worked up. The crude product is chromatographed over 400 g of silica gel (500 ml fractions), fractions 1-12 being eluted with toluene/ethyl acetate (1:1), fractions 13-19 with toluene/ethyl acetate (2:3) and the later fractions with ethyl acetate. By reprecipitating fractions 14-25 from CH2Cl2 /ether/hexane, 3-acetoxymethyl-7β-{(2S)-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 =19°±1° (0.96% in CHCl3), IR: 3570, 3400, 1795, 1750-1700 (wide), 1620, 1608, 1510 cm-1 (CH2Cl2).

Workup

  1. customThe crude product is chromatographed over 400 g of silica gel (500 ml fractions), fractions 1-12
  2. washbeing eluted with toluene/ethyl acetate (1:1), fractions 13-19 with toluene/ethyl acetate (2:3)
  3. customBy reprecipitating fractions 14-25 from CH2Cl2 /ether/hexane

Sources & evidence

ORD record
ord-c34bc85ab17349909d896afa30fe672c
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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