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

HRID 1729557Notes

Reaction equation

HRID 1729557 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][C:66]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)/[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][C:66]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)([C:73]2[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=2)[C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)/[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:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 10327150(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic AcidHCID 131718602Diphenylmethyl 7-amino-3-(tetrahydropyran-2-yl)methylthio-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 141573512O-benzhydryl (6R)-3-(oxan-2-ylmethyl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioateYield 60%

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-trityloxyiminoacetic acid (403 mg) in accordance with the procedure of Example 1(d). The crude reaction product was purified by a column chromatography on a silica gel column (30 g) with elution using benzene-ethyl acetate (7:1 by volume) as eluent to collect fractions containing the titled compound. Concentration of the fractions so collected gave the titled compound (380 mg; 60%).

Workup

  1. customThe crude reaction product
  2. customwas purified by a column chromatography on a silica gel column (30 g) with elution
  3. customto collect fractions
  4. additioncontaining the titled compound
  5. customConcentration of the fractions so collected

Sources & evidence

ORD record
ord-64852ca485b14519afaae9a2b1594390
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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