Acetonitrile → HCID 88720460, compound

HRID 358160Notes

Reaction equation

HRID 358160 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](C4C=CC(C(OC(C)(C)C)=O)=CC=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][S:58][C:59]2[N:63]([CH3:64])[N:62]=[N:61][N:60]=2)=[O:16])C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[C:66]1([CH3:76])[CH:71]=[CH:70][C:69]([S:72]([OH:75])(=[O:74])=[O:73])=[CH:68][CH:67]=1.[C:77](#[N:79])[CH3:78]>>[C:66]1([CH3:76])[CH:67]=[CH:68][C:69]([S:72]([OH:75])(=[O:73])=[O:74])=[CH:70][CH:71]=1.[C:66]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:1]4[CH:2]=[CH:3][C:77]([NH2:79])=[CH:78][CH:6]=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][S:58][C:59]2[N:63]([CH3:64])[N:62]=[N:61][N:60]=2)=[O:16])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 521998p-Toluenesulfonic acid monohydrateHCID 131713646HCID 131713646, compound

Product 1

HCID 88720460HCID 88720460, compound

Procedure

In the manner described in Example 11, 3.40 g of 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7β-[(2R)-2-(4-BOC-aminophenyl)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-acetamido]-3-cephem-4-carboxylic acid diphenylmethyl ester are reacted with 1.38 g of p-toluenesulphonic acid monohydrate in 30 ml of acetonitrile and worked up. 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 is obtained. [α]D20 =-32°±1° (0.96% in DMSO).

Sources & evidence

ORD record
ord-daaa407814234cd9b16f049ba877ff64
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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