HCID 19022435, compound → HCID 88442879, compound

HRID 1109342Notes

Reaction equation

[NH2:1][O:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([OH:14])[C:10](=[CH:12][CH:13]=1)[OH:11])(=[O:6])=[O:5].[NH2:15][C:16]1[S:17][CH:18]=[C:19]([C:21](=O)[C:22]([NH:24][C@@H:25]2[C:32](=[O:33])[N:31]3[C@@H:26]2[S:27][CH2:28][C:29]([CH2:37][S:38][C:39]2[CH:44]=[C:43]([CH3:45])[N:42]4[N:46]=[CH:47][C:48]([C:49]([OH:51])=[O:50])=[C:41]4[N:40]=2)=[C:30]3[C:34]([OH:36])=[O:35])=[O:23])[N:20]=1>>[NH2:15][C:16]1[S:17][CH:18]=[C:19](/[C:21](=[N:1]/[O:2][CH2:3][S:4]([C:7]2[CH:13]=[CH:12][C:10]([OH:11])=[C:9]([OH:14])[CH:8]=2)(=[O:5])=[O:6])/[C:22]([NH:24][C@@H:25]2[C:32](=[O:33])[N:31]3[C@@H:26]2[S:27][CH2:28][C:29]([CH2:37][S:38][C:39]2[CH:44]=[C:43]([CH3:45])[N:42]4[N:46]=[CH:47][C:48]([C:49]([OH:51])=[O:50])=[C:41]4[N:40]=2)=[C:30]3[C:34]([OH:36])=[O:35])=[O:23])[N:20]=1

Participants

Reactant 2

HCID 19022435HCID 19022435, compound

HCID 86744946HCID 86744946, compound

Product 1

HCID 88442879HCID 88442879, compound

Procedure

307 mg of 4-[[(aminooxy)methyl]sulphonyl]pyrocatechol were reacted with 575 mg of (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[(3-carboxy-7-methylpyrazolo[1,5-a]pyrimidin-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in an analogous manner to the procedure described in Examples 11 or 7. There was obtained (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[(3-carboxy-7-methylpyrazolo[1,5-a]pyrimidin-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white powder.

Sources & evidence

ORD record: ord-1080dcdb0ae8443a87a06a516cdfdd6b
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05319140

Reaction notes

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