Sodium Hydroxide → Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

HRID 435459Notes

Reaction equation

HRID 435459 reaction equation
C[C@@H]1O[C@@H]([O:8][CH:9]2[C@@H:14]([N:15]([CH3:17])[CH3:16])[CH2:13][C@H:12]([O:18][C@@H:19]3[C:24]4[C:25]([OH:40])=[C:26]5[C:33](=[O:34])[C:32]6[C:35]([OH:39])=[CH:36][CH:37]=[CH:38][C:31]=6[C:29](=[O:30])[C:27]5=[CH:28][C:23]=4[C@@H:22]([C:41]([O:43][CH3:44])=[O:42])[C@@:21]([OH:46])([CH3:45])[CH2:20]3)[O:11][C@H:10]2[CH3:47])C[C@H](O)[C@@H]1O.[OH-].[Na+]>Cl>[CH3:47][CH:10]1[O:11][CH:12]([O:18][CH:19]2[C:24]3[C:25]([OH:40])=[C:26]4[C:33](=[O:34])[C:32]5[C:35]([OH:39])=[CH:36][CH:37]=[CH:38][C:31]=5[C:29](=[O:30])[C:27]4=[CH:28][C:23]=3[CH:22]([C:41]([O:43][CH3:44])=[O:42])[C:21]([OH:46])([CH3:45])[CH2:20]2)[CH2:13][CH:14]([N:15]([CH3:17])[CH3:16])[CH:9]1[OH:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 174332Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-{[2,3,6-trideoxy-4-O-(2,6-dideoxyhexopyranosyl)-3-(dimethylamino)hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Product 1

HCID 174252Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylateYield 88.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 100 mg of auramycin C in 50 ml of 0.5% hydrochloric acid was hydrolysed at room temperature for 60 minutes. The reaction mixture was neutralised by dilute sodium hydroxide solution, extracted with 100 ml of chloroform twice and concentrated in vacuo to a small volume. The concentrate was chromatographed with thin layer chromatography plates (chloroform:methanol, 5:1). The band containing auramycin D was scraped off and extracted with a solvent mixture of chloroform and methanol (4:1) and concentrated in vacuo to dryness yielding 72 mg of auramycin D.

Workup

  1. extractionextracted with 100 ml of chloroform twice
  2. concentrationconcentrated in vacuo to a small volume
  3. customThe concentrate was chromatographed with thin layer chromatography plates (chloroform:methanol, 5:1)
  4. additionThe band containing auramycin D
  5. extractionextracted with a solvent mixture of chloroform and methanol (4:1)
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-0236c0a4f7814ab48b29a0c6e6710b77
Source dataset
uspto-grants-1983_08
Patent number
US04401812

Reaction notes

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