Acetaldehyde → Netilmicin

HRID 1415073

Reaction equation

HRID 1415073 reaction equation
S(=O)(=O)(O)O.[CH3:6][C@@:7]1([OH:36])[C@H:12]([NH:13][CH3:14])[C@@H:11]([OH:15])[C@@H:10]([O:16][C@@H:17]2[C@@H:22]([OH:23])[C@H:21]([O:24][C@H:25]3[O:30][C:29]([CH2:31][NH2:32])=[CH:28][CH2:27][C@H:26]3[NH2:33])[C@@H:20]([NH2:34])[CH2:19][C@H:18]2[NH2:35])[O:9][CH2:8]1.F[C:38](F)(F)[C:39](O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.P(=O)(O)(O)O.[N+]([O-])(O)=O.C(=O)C.C([BH3-])#N.[Na+]>O.C(O)(=O)C>[CH3:38][CH2:39][NH:35][C@H:18]1[C@H:17]([O:16][C@H:10]2[O:9][CH2:8][C@@:7]([OH:36])([CH3:6])[C@H:12]([NH:13][CH3:14])[C@H:11]2[OH:15])[C@@H:22]([OH:23])[C@H:21]([O:24][C@H:25]2[O:30][C:29]([CH2:31][NH2:32])=[CH:28][CH2:27][C@H:26]2[NH2:33])[C@@H:20]([NH2:34])[CH2:19]1

Participants

12

Reactant 9

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 6422Trifluoroacetic acidHCID 36119SisomicinHCID 5003444Sodium cyanoborohydride

Product 1

HCID 441306Netilmicin

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

in the procedure of above Example 1A instead of adding 1 N sulfuric acid to the solution of sisomicin in water until it reaches a pH of about 5, other acids may be used, such as acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, hydrochloric acid, phosphoric acid, or nitric acid. The acidified aqueous solution is then treated with acetaldehyde and sodium cyanoborohydride and the resultant product is purified as described above, whereby is obtained 1-N-ethylsisomicin.

Workup

  1. customthe resultant product is purified

Sources & evidence

ORD record
ord-1cf3e61ee5494d7a91ba96e414aab62f
Source dataset
uspto-grants-1977_01
Patent number
US04002742

Linked notes

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