Diethyl Ether → HCID 131713642, compound

HRID 358159Notes

Reaction equation

HRID 358159 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:52])[C@@H:24]([NH:25][C:26](=[O:51])[C@@H:27]([C:37]4[CH:42]=[CH:41][C:40](C(OC(C)(C)C)=O)=[CH:39][C:38]=4N)[NH:28][C:29]([N:31]4[CH2:35][C:34](=[O:36])[N:33]=[C-:32]4)=[O:30])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:53][S:54][C:55]2[N:59]([CH3:60])[N:58]=[N:57][N:56]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:62]1([CH3:72])[CH:67]=[CH:66][C:65]([S:68]([OH:71])(=[O:70])=[O:69])=[CH:64][CH:63]=1.CCOCC.C(#[N:80])C>>[C:62]1([CH3:72])[CH:63]=[CH:64][C:65]([S:68]([O-:71])(=[O:69])=[O:70])=[CH:66][CH:67]=1.[C:8]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:52])[C@@H:24]([NH:25][C:26](=[O:51])[C@@H:27]([C:37]4[CH:42]=[CH:41][C:40]([NH2:80])=[CH:39][CH:38]=4)[NH:28][C:29]([N:31]4[CH2:35][C:34](=[O:36])[N:33]=[C-:32]4)=[O:30])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:53][S:54][C:55]2[N:59]([CH3:60])[N:58]=[N:57][N:56]=2)=[O:16])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 131713644HCID 131713644, compound

Product 1

HCID 131713642HCID 131713642, compound

Procedure

5 g of 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7β-[(2R)-2-(4-BOC-aminophenyl)-2-(2-imidazolidone-1-carboxamido)-acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester are stirred at room temperature for 21/2 hours with 2.3 g of p-toluenesulphonic acid monohydrate in 50 ml of acetonitrile. After adding 500 ml of ether, filtering the precipitate with suction, washing with 300 ml of ether and drying in vacuo, 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7β-[(2R)-2-(4-aminophenyl)-2-(2-imidazolidone-1-carboxamido)-acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester p-toluenesulphonate is obtained [α]D20 =-37°±1° (0.758% in CH3OH).

Workup

  1. filtrationfiltering the precipitate with suction
  2. washwashing with 300 ml of ether
  3. customdrying in vacuo

Sources & evidence

ORD record
ord-5b43ae5db19d4af28f464b26a569882f
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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