Hydrochloric Acid → N-Acetylbenanomicin B

HRID 2371378Notes

Reaction equation

HRID 2371378 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C:18]3[C:13](=[C:14]([OH:28])[C:15]([C:20]([NH:22][C@@H:23]([C:25]([OH:27])=[O:26])[CH3:24])=[O:21])=[C:16]([CH3:19])[CH:17]=3)[C:12]3[C:29]([OH:46])=[C:30]4[C:41](=[O:42])[C:40]5[C:35](=[C:36]([OH:45])[CH:37]=[C:38]([O:43][CH3:44])[CH:39]=5)[C:33](=[O:34])[C:31]4=[CH:32][C:11]=3[C@@H:10]2[OH:47])[C@H:5]([OH:48])[C@@H:4]([O:49][C@@H:50]2[O:55][CH2:54][C@@H:53]([OH:56])[C@H:52]([OH:57])[C@H:51]2[OH:58])[C@H:3]1[NH2:59].Cl.[C:61](OC(=O)C)(=[O:63])[CH3:62].Cl.C[C@H]1O[C@@H](O[C@H]2C3C(=C(O)C(C(NC(C(O)=O)C)=O)=C(C)C=3)C3C(O)=C4C(=O)C5C(=C(O)C=C(OC)C=5)C(=O)C4=CC=3[C@@H]2O)[C@H](O)[C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H]1N>C(=O)([O-])[O-].[Na+].[Na+].CO>[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C:18]3[C:13](=[C:14]([OH:28])[C:15]([C:20]([NH:22][C@@H:23]([C:25]([OH:27])=[O:26])[CH3:24])=[O:21])=[C:16]([CH3:19])[CH:17]=3)[C:12]3[C:29]([OH:46])=[C:30]4[C:41](=[O:42])[C:40]5[C:35](=[C:36]([OH:45])[CH:37]=[C:38]([O:43][CH3:44])[CH:39]=5)[C:33](=[O:34])[C:31]4=[CH:32][C:11]=3[C@@H:10]2[OH:47])[C@H:5]([OH:48])[C@@H:4]([O:49][C@@H:50]2[O:55][CH2:54][C@@H:53]([OH:56])[C@H:52]([OH:57])[C@H:51]2[OH:58])[C@H:3]1[NH:59][C:61]([CH3:62])=[O:63]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 441180HCID 441180, compoundHCID 5748955Benanomicin B hydrochloride

Product 1

HCID 5479153N-Acetylbenanomicin B

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

Benanomicin B hydrochloride (125 mg) was dissolved in 10 ml of an aqueous solution of 0.1 M sodium carbonate, and to the resulting solution was added 0.1 ml of acetic anhydride. The mixture obtained was stirred at ambient temperature for 20 minutes. The resultant reaction solution was then adjusted to pH 4.0 by addition of 1 M hydrochloric acid and subsequently passed through a column of 20 ml of a non-ionic microporous adsorbent resin, "Diaion" HP-20 (a product of Mitsubishi Kasei Co., Japan) to adsorb the acetylation product of benanomicin B by the resin. The resin column was washed with water and developed with aqueous 80% acetone. The red colored fractions of the eluate were combined together and concentrated to dryness. The residue obtained was dissolved in methanol and the methanolic solution was passed through a column of a molecule-sieve agent, "Sephadex" LH-20 (a product of Pharmacia Co., Sweden), followed by developement with methanol. The eluate which showed a single spot of red color on a thin layer chromatography on a silica gel plate was concentrated to dryness. N-acetylbenanomicin B (118 mg) was obtained as a reddish brown colored powder which showed a melting point of higher than 200° C.

Workup

  1. customThe mixture obtained
  2. customThe resultant reaction solution
  3. washThe resin column was washed with water
  4. concentrationconcentrated to dryness
  5. customThe residue obtained
  6. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-abcb11456f7d4fe087845ce937b655d9
Source dataset
uspto-grants-1992_03
Patent number
US05093323

Reaction notes

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