HCID 19022435, compound → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3,4-dihydroxyphenyl)sulfonylmethoxyimino]acetyl]amino]-3-[[3-carbamoyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 846893Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[N:28]4[N:35]=[CH:36][C:37]([C:38](=[O:40])[NH2:39])=[C:27]4[N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.[O:42]([CH2:44][S:45]([C:48]1[CH:49]=[C:50]([OH:55])[C:51](=[CH:53][CH:54]=1)[OH:52])(=[O:47])=[O:46])[NH2:43]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:42][CH2:44][S:45]([C:48]2[CH:54]=[CH:53][C:51]([OH:52])=[C:50]([OH:55])[CH:49]=2)(=[O:46])=[O:47])/[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[CH:30]=[C:29]([C:31]([F:33])([F:32])[F:34])[N:28]4[N:35]=[CH:36][C:37]([C:38](=[O:40])[NH2:39])=[C:27]4[N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

Reactant 2

HCID 19022435HCID 19022435, compound

HCID 86745299(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(3-carbamoyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 88442887(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(3,4-dihydroxyphenyl)sulfonylmethoxyimino]acetyl]amino]-3-[[3-carbamoyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(3-carbamoyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was reacted with 4-[[(aminoxy)methyl]-sulphonyl]pyrocatechol according to the procedure described in Example 7. After purification of the product with the chromatographic procedure in Example 7 and lyophilization of the product, there was obtained (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)-sulphonyl]methoxy]imino]acetamido]-3-[[(3-carbamoyl-7-(tri-fluoromethyl)pyrazolo[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 pale yellow powder.

Workup

customAfter purification of the product with the chromatographic procedure in Example 7 and lyophilization of the product

Sources & evidence

ORD record: ord-8bb45b88d5a64051b2a1248f274a8dd9
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05138066

Reaction notes

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