3-Aminorifamycin S → 3-Amino-rifamycin

HRID 1703454Notes

Reaction equation

HRID 1703454 reaction equation
[CH3:1][C@@H:2]1[C@H:37]([OH:38])[C@@H:36]([CH3:39])[C@@H:35]([OH:40])[C@@H:34]([CH3:41])[C@H:33]([O:42][C:43]([CH3:45])=[O:44])[C@H:32]([CH3:46])[C@@H:31]([O:47][CH3:48])[CH:30]=[CH:29][O:28][C@:25]2([CH3:49])[C:26](=[O:27])[C:15]3[C:16]([O:24]2)=[C:17]([CH3:23])[C:18]([OH:22])=[C:19]2[C:20](=[O:21])[C:10](=[C:11]([NH2:50])[C:12]([C:14]=32)=[O:13])[NH:9][C:7](=[O:8])[C:6]([CH3:51])=[CH:5][CH:4]=[CH:3]1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>COCCOCCOC.O>[CH3:1][C@@H:2]1[C@H:37]([OH:38])[C@@H:36]([CH3:39])[C@@H:35]([OH:40])[C@@H:34]([CH3:41])[C@H:33]([O:42][C:43]([CH3:45])=[O:44])[C@H:32]([CH3:46])[C@@H:31]([O:47][CH3:48])[CH:30]=[CH:29][O:28][C@:25]2([CH3:49])[C:26](=[O:27])[C:15]3=[C:16]([O:24]2)[C:17]([CH3:23])=[C:18]([OH:22])[C:19]2=[C:14]3[C:12]([OH:13])=[C:11]([NH2:50])[C:10](=[C:20]2[OH:21])[NH:9][C:7](=[O:8])[C:6]([CH3:51])=[CH:5][CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 128896223-Aminorifamycin SHCID 23667548Sodium Ascorbate

Product 1

HCID 1018722523-Amino-rifamycin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

8 g 3-amino-rifamycin S were dissolved in 30 ml diglyme and the solution was then added with 2 g sodium ascorbate dissolved in 5 ml water. The solution of 3-amino-rifamycin SV thus obtained was heated to 50° C. and then added with 4.4 g 4-carboxybenzoic aldehyde. The solution was stirred at this temperature for 15 minutes and then after adding 30 ml chloroform was again stirred at 50° C. for 4 hours. The reaction mixture was then added with 300 ml chloroform, washed with an aqueous solution of sodium metabisulphite and then with water.

Sources & evidence

ORD record
ord-5a37a17dc0aa42eca211daa83be04c80
Source dataset
uspto-grants-1978_11
Patent number
US04124586

Reaction notes

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