(4-methoxyphenyl)methyl (6R)-3-(chloromethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → (4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-([1,3]thiazolo[4,5-b]pyridin-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 128871Notes

Reaction equation

HRID 128871 reaction equation
[SH:1][C:2]1[S:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[C:11]([NH:30][C:31]1[S:32][CH:33]=[C:34](/[C:36](=[N:63]/[O:64][CH3:65])/[C:37]([NH:39][CH:40]2[C:61](=[O:62])[N:42]3[C:43]([C:49]([O:51][CH2:52][C:53]4[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=4)=[O:50])=[C:44]([CH2:47]Cl)[CH2:45][S:46][C@H:41]23)=[O:38])[N:35]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:11]([NH:30][C:31]1[S:32][CH:33]=[C:34](/[C:36](=[N:63]/[O:64][CH3:65])/[C:37]([NH:39][CH:40]2[C:61](=[O:62])[N:42]3[C:43]([C:49]([O:51][CH2:52][C:53]4[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=4)=[O:50])=[C:44]([CH2:47][S:1][C:2]4[S:3][C:4]5[C:5]([N:10]=4)=[N:6][CH:7]=[CH:8][CH:9]=5)[CH2:45][S:46][C@H:41]23)=[O:38])[N:35]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 88174722(4-methoxyphenyl)methyl (6R)-3-(chloromethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178527821HCID 178527821, compound

Product 1

HCID 141566713(4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-([1,3]thiazolo[4,5-b]pyridin-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 62%

Procedure

Using 111 mg of 2-mercaptothiazolo[4,5-b]pyridine in place of 2-mercaptothiazolo[4,5-c]pyridine and 477 mg of p-methoxybenzyl 7-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido}-3-chloromethyl-3-cephem-4-carboxylate, the reaction and purification were carried out in the same manner as in Example 1(a) to obtain 345 mg of the title compound in a yield of 62%.

Workup

  1. customthe reaction and purification

Sources & evidence

ORD record
ord-b43a4316df344b0b8c26282707141ae1
Source dataset
uspto-grants-1995_11
Patent number
US05464829

Reaction notes

Loading…