Sodium Nitrite → HCID 178483106, compound

HRID 1448034Notes

Reaction equation

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

Participants

Reactant 2

HCID 23668193Sodium Nitrite

HCID 88790604HCID 88790604, compound

Product 1

HCID 178483106HCID 178483106, compoundYield 88.7%

Procedure

By the same procedure as described in Example 1, 0.378 g of benzhydryl 7-(4-bromo-3-oxobutyrylamino)-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate was treated with 0.048 g of sodium nitrite to obtain 0.350 g powdery benzhydryl 7-(4-bromo-3-oxo-2-hydroxyiminobutyrylamino)-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate (syn-isomer).

Sources & evidence

ORD record: ord-278a575ddb884034b363534349c2ea69
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04179502

Reaction notes

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