Water → N-Acetylelsamicin A

HRID 1492684Notes

Reaction equation

HRID 1492684 reaction equation
[CH3:1][C@H:2]1[O:7][C@H:6]([O:8][C@@H:9]2[C@:14]([OH:16])([CH3:15])[C@@H:13]([OH:17])[C@@H:12]([CH3:18])[O:11][C@H:10]2[O:19][C:20]2[C:25]3[C:26]4[O:36][C:34](=[O:35])[C:33]5[C:28]6=[C:29]([O:38][C:39]([C:41](=[C:42]([OH:43])[C:24]=3[CH:23]=[CH:22][CH:21]=2)[C:27]=46)=[O:40])[CH:30]=[CH:31][C:32]=5[CH3:37])[C@H:5]([NH2:44])[C@@H:4]([O:45][CH3:46])[C@H:3]1[OH:47].[C:48](OC(=O)C)(=[O:50])[CH3:49].O>CO>[CH3:1][C@H:2]1[O:7][C@H:6]([O:8][C@@H:9]2[C@:14]([OH:16])([CH3:15])[C@@H:13]([OH:17])[C@@H:12]([CH3:18])[O:11][C@H:10]2[O:19][C:20]2[C:25]3[C:26]4[O:36][C:34](=[O:35])[C:33]5[C:28]6=[C:29]([O:38][C:39]([C:41](=[C:42]([OH:43])[C:24]=3[CH:23]=[CH:22][CH:21]=2)[C:27]=46)=[O:40])[CH:30]=[CH:31][C:32]=5[CH3:37])[C@H:5]([NH:44][C:48]([CH3:49])=[O:50])[C@@H:4]([O:45][CH3:46])[C@H:3]1[OH:47]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 5362259Elsamitrucin

Product 1

HCID 5489393N-Acetylelsamicin AYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of elsamicin A (65.4 mg) and acetic anhydride (0.1 ml) in dry methanol (2 ml) was stirred at room temperature for 1 hour. Water (1 ml) was added and the mixture was evaporated in vacuo to give a yellow oil, which was purified by column chromatography on silica gel to give 70.5 mg (100%) of the desired product.

Workup

  1. customthe mixture was evaporated in vacuo
  2. customto give a yellow oil, which
  3. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ecb0420e554545c3bea50f8c982cebf2
Source dataset
uspto-grants-1994_12
Patent number
US05374711

Reaction notes

Loading…