Acetonitrile → HCID 88720709, compound

HRID 358165Notes

Reaction equation

HRID 358165 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:56])[C@@H:24]([NH:25][C:26](=[O:55])[C@H:27]([C:41]4[CH:46]=[CH:45][C:44](C(OC(C)(C)C)=O)=[CH:43][C:42]=4N)[NH:28][C:29]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[C:33](=[O:39])[C:32]4=[O:40])=[O:30])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:57][O:58][C:59](=[O:61])[NH2:60])=[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:63]1([CH3:73])[CH:68]=[CH:67][C:66]([S:69]([OH:72])(=[O:71])=[O:70])=[CH:65][CH:64]=1.C(#[N:76])C>>[C:63]1([CH3:73])[CH:64]=[CH:65][C:66]([S:69]([OH:72])(=[O:70])=[O:71])=[CH:67][CH:68]=1.[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:56])[C@@H:24]([NH:25][C:26](=[O:55])[C@H:27]([C:41]4[CH:42]=[CH:43][C:44]([NH2:76])=[CH:45][CH:46]=4)[NH:28][C:29]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[C:33](=[O:39])[C:32]4=[O:40])=[O:30])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:57][O:58][C:59](=[O:61])[NH2:60])=[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

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 131713650HCID 131713650, compound

Product 1

HCID 88720709HCID 88720709, compound

Procedure

3.3 g of 7β-[(2S)-2-(4-BOC-aminophenyl)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid diphenylmethyl ester are reacted in 100 ml of acetonitrile with 1.46 g of p-toluenesulphonic acid monohydrate in the manner described in Example 22. 7β-[(2S)-2-(4-Aminophenyl)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid diphenylmethyl ester p-toluenesulphonate is obtained. [α]D20 =+27°±1° (0.954% in CH3OH);

Sources & evidence

ORD record
ord-3ed1cd25ff56482c9b1ac22cf62d2b29
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

Loading…