Sodium Azide → HCID 131713101, compound

HRID 1995806Notes

Reaction equation

HRID 1995806 reaction equation
Br[CH2:2][C:3]([NH:5][C@@H:6]1[C:18](=[O:19])[N:8]2[C:9]([C:15]([OH:17])=[O:16])=[C:10]([O:13][CH3:14])[CH2:11][S:12][C@H:7]12)=[O:4].[N-:20]=[N+:21]=[N-:22].[Na+]>C(O)C.O>[N:20]([CH2:2][C:3]([NH:5][C@@H:6]1[C:18](=[O:19])[N:8]2[C:9]([C:15]([OH:17])=[O:16])=[C:10]([O:13][CH3:14])[CH2:11][S:12][C@H:7]12)=[O:4])=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 70502609HCID 70502609, compound

Product 1

HCID 131713101HCID 131713101, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution, prepared at 30° C., of 7β-bromoacetylamino-3-methoxy-3-cephem-4-carboxylic acid (about 0.15 mmol), prepared according to the process described in Example 43, in 10 ml of ethanol and 0.3 ml of water is mixed with a solution of 0.03 g of sodium azide in 0.5 ml of water. The reaction mixture is stirred for 15 hours at room temperature with exclusion of light and is then worked up according to the process described in Example 41. 7β-Azidoacetylamino-3-methoxy-3-cephem-4-carboxylic acid is thus obtained, which in a thin layer chromatogram (silica gel; system: n-butanol/pyridine/acetic acid/water, 42:24:4:30) shows an Rf value of 0.40; ultraviolet absorption spectrum (in ethanol): λmax at 264 mμ; infrared absorption spectrum (in mineral oil): characteristic bands at 4.65μ and 5.64μ.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-15958ef9d2ef4b3ebef891b0b6826ef4
Source dataset
uspto-grants-1983_09
Patent number
US04405778

Reaction notes

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