(4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → HCID 178491526, compound

HRID 128882Notes

Reaction equation

HRID 128882 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:53]/[O:54][C@H:55]([C:57]([O:59][CH:60]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:58])[CH3:56])/[C:27]([NH:29][CH:30]2[C:51](=[O:52])[N:32]3[C:33]([C:39]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=4)=[O:40])=[C:34]([CH2:37]Cl)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:73][C:74]([F:79])([F:78])[C:75]([O-:77])=[O:76].[CH3:80][N+:81]1[C:82]([SH:91])=[N:83][C:84]2[C:89]=1[CH:88]=[CH:87][N:86]([CH3:90])[CH:85]=2>>[F:73][C:74]([F:79])([F:78])[C:75]([O-:77])=[O:76].[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:53]/[O:54][C@H:55]([C:57]([O:59][CH:60]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:58])[CH3:56])/[C:27]([NH:29][CH:30]2[C:51](=[O:52])[N:32]3[C:33]([C:39]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=4)=[O:40])=[C:34]([CH2:37][S:91][C:82]4[N+:81]([CH3:80])=[C:89]5[CH:88]=[CH:87][N:86]([CH3:90])[CH:85]=[C:84]5[N:83]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 88420502(4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178480134HCID 178480134, compound

Product 1

HCID 178491526HCID 178491526, compoundYield 88%

Procedure

Using 306 mg of p-methoxybenzyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-{(S)-1-diphenylmethoxycarbonylethoxyimino}acetamido]-3-chloromethyl-3-cephem-4-carboxylate and 153 mg of 1,5-dimethyl-2-mercaptoimidazolo[4,5-c]pyridinium trifluoroacetate in place of p-methoxybenzyl 7-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido}-3-chloromethyl-3-cephem-4-carboxylate and 2-mercapto-4-methylthiazolo[5,4-b]pyridinium trifluoroacetate, respectively, the reaction and purification were carried out in the same manner as in Example 15(a) to obtain 334 mg of the title compound in a yield of 88%.

Workup

  1. customrespectively, the reaction and purification

Sources & evidence

ORD record
ord-20c5c5b208fe4b55a1ae70b04fed64ce
Source dataset
uspto-grants-1995_11
Patent number
US05464829

Reaction notes

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