(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic Acid → O-benzhydryl (6R)-3-(oxan-4-yl)-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 1729551Notes

Reaction equation

HRID 1729551 reaction equation
Cl.[NH2:2][CH:3]1[C:32](=[O:33])[N:5]2[C:6]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[S:17])=[C:7]([CH:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[CH2:8][S:9][C@H:4]12.[C:34]([NH:53][C:54]1[S:55][CH:56]=[C:57](/[C:59](=[N:63]/[O:64][C:65]([C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)/[C:60](O)=[O:61])[N:58]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[C:34]([NH:53][C:54]1[S:55][CH:56]=[C:57](/[C:59](=[N:63]/[O:64][C:65]([C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)([C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=2)[C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=2)/[C:60]([NH:2][CH:3]2[C:32](=[O:33])[N:5]3[C:6]([C:16]([O:18][CH:19]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[S:17])=[C:7]([CH:10]4[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)[CH2:8][S:9][C@H:4]23)=[O:61])[N:58]=1)([C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 10327150(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic AcidHCID 131718592Diphenylmethyl 7-amino-3-(tetrahydropyran-4-yl)thio-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 141559363O-benzhydryl (6R)-3-(oxan-4-yl)-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 88%

Procedure

Diphenylmethyl 7-amino-3-(tetrahydropyran-4-yl)thio-3-cephem-4-carboxylate hydrochloride (290 mg) was reacted with (Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetic acid (403 mg), followed by purifying the reaction product in accordance with the procedure of Example 1(d), affording the titled compound (500 mg; 88%).

Workup

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

Sources & evidence

ORD record
ord-d43cb5a5d6864fc79645927013bb6c17
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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