Triethylamine → (4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(1R)-2-benzhydryloxy-1-(3,4-dihydroxyphenyl)-2-oxoethoxy]imino-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

HRID 1654560Notes

Reaction equation

HRID 1654560 reaction equation
[CH:1]([O:14][C:15]([C@H:17]([O:26]/[N:27]=[C:28](/[C:32]1[N:33]=[C:34]([NH:37][C:38]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[S:35][CH:36]=1)\[C:29](O)=[O:30])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:25])[CH:19]=1)=[O:16])([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.[NH2:57][CH:58]1[C:79](=[O:80])[N:60]2[C:61]([C:67]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][C:74]([O:77][CH3:78])=[CH:73][CH:72]=3)=[O:68])=[C:62]([CH2:65][Cl:66])[CH2:63][S:64][C@H:59]12.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>>[CH:1]([O:14][C:15]([C@H:17]([O:26]/[N:27]=[C:28](/[C:32]1[N:33]=[C:34]([NH:37][C:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[S:35][CH:36]=1)\[C:29]([NH:57][CH:58]1[C:79](=[O:80])[N:60]2[C:61]([C:67]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][C:74]([O:77][CH3:78])=[CH:73][CH:72]=3)=[O:68])=[C:62]([CH2:65][Cl:66])[CH2:63][S:64][C@H:59]12)=[O:30])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:25])[CH:19]=1)=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 140320224-Methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylateHCID 15780328(2Z)-2-[(1R)-2-benzhydryloxy-1-(3,4-dihydroxyphenyl)-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid

Product 1

HCID 16183830(4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(1R)-2-benzhydryloxy-1-(3,4-dihydroxyphenyl)-2-oxoethoxy]imino-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-carboxylateYield 100.7%

Procedure

By using 4.57 g (6 mmol) of (Z)-2-[[(R)-α-benzhydryloxycarbonyl-3,4-dihydroxybenzyl]oxyimino]-2-(2-tritylaminothiazol-4-yl)acetic acid, 2.03 g (5 mmol) of p-methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate, 1.39 ml (10 mmol) and 0.84 ml (6 mmol) of triethylamine and 0.75 ml (8 mmol) of phosphorus oxychloride, the treatment was conducted in the same manner as in Example 1 (A) to obtain 5.60 g (yield: 56%) of p-methoxybenzyl 7-[(Z)-2-[[(R)-α-benzhydryloxycarbonyl-3,4-dihydroxybenzyl]oxyimino]-2-(tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate as a foam-like solid.

Sources & evidence

ORD record
ord-6d2a507f3f194e5d81765677f42080cb
Source dataset
uspto-grants-1995_04
Patent number
US05407930

Reaction notes

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