(Z)-2-methoxymino-2-(2-(tritylamino)thiazol-4-yl)acetic acid → O-benzhydryl (6R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(oxan-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate

HRID 1729555Notes

Reaction equation

HRID 1729555 reaction equation
Cl.[NH2:2][CH:3]1[C:33](=[O:34])[N:5]2[C:6]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[S:18])=[C:7]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH2:8][S:9][C@H:4]12.[C:35]([NH:54][C:55]1[S:56][CH:57]=[C:58](/[C:60](=[N:64]/[O:65][CH3:66])/[C:61](O)=[O:62])[N:59]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[C:35]([NH:54][C:55]1[S:56][CH:57]=[C:58](/[C:60](=[N:64]/[O:65][CH3:66])/[C:61]([NH:2][CH:3]2[C:33](=[O:34])[N:5]3[C:6]([C:17]([O:19][CH:20]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[S:18])=[C:7]([CH2:10][CH:11]4[CH2:16][CH2:15][CH2:14][CH2:13][O:12]4)[CH2:8][S:9][C@H:4]23)=[O:62])[N:59]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 5928144(Z)-2-methoxymino-2-(2-(tritylamino)thiazol-4-yl)acetic acidHCID 131718602Diphenylmethyl 7-amino-3-(tetrahydropyran-2-yl)methylthio-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 141573513O-benzhydryl (6R)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(oxan-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioateYield 78%

Procedure

Diphenylmethyl 7-amino-3-(tetrahydropyran-2-yl)methylthio-3-cephem-4-carboxylate hydrochloride (300 mg) was reacted with (Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid (267 mg), followed by purifying the reaction product in accordance with the procedure of Example 1(d), affording the titled compound (360 mg; 78%).

Workup

  1. customby purifying the reaction product in accordance with the procedure of Example 1(d)

Sources & evidence

ORD record
ord-e5d512eea49c478e9c887ce8cf224823
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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