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 435456Notes

Reaction equation

HRID 435456 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3[C:15]([OH:30])=[C:16]4[C:23](=[O:24])[C:22]5[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:21]=5[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[C@@H:12]([C:31]([O:33][CH3:34])=[O:32])[C@@:11]([OH:36])([CH3:35])[CH2:10]2)[CH2:5][C@H:4]([N:37]([CH3:39])[CH3:38])[C@@H:3]1[O:40][C@@H:41]1[O:46][C@@H:45]([CH3:47])[C@@H:44]([O:48][C@@H]2O[C@@H](C)C(=O)CC2)[C@@H:43]([OH:57])[CH2:42]1.[OH-].[Na+]>Cl>[CH3:47][C@@H:45]1[O:46][C@@H:41]([O:40][CH:3]2[C@@H:4]([N:37]([CH3:38])[CH3:39])[CH2:5][C@H:6]([O:8][C@@H:9]3[C:14]4[C:15]([OH:30])=[C:16]5[C:23](=[O:24])[C:22]6[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:21]=6[C:19](=[O:20])[C:17]5=[CH:18][C:13]=4[C@@H:12]([C:31]([O:33][CH3:34])=[O:32])[C@@:11]([OH:36])([CH3:35])[CH2:10]3)[O:7][C@H:2]2[CH3:1])[CH2:42][C@H:43]([OH:57])[C@@H:44]1[OH:48].[CH3:1][CH:2]1[O:7][CH:6]([O:8][CH:9]2[C:14]3[C:15]([OH:30])=[C:16]4[C:23](=[O:24])[C:22]5[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:21]=5[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[CH:12]([C:31]([O:33][CH3:34])=[O:32])[C:11]([OH:36])([CH3:35])[CH2:10]2)[CH2:5][CH:4]([N:37]([CH3:39])[CH3:38])[CH:3]1[OH:40]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 155838Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-({2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-(6-methyl-5-oxooxan-2-yl)hexopyranosyl]-3-(dimethylamino)hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Product 2

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-carboxylateHCID 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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 100 mg of auramycin A in 50 ml of 0.5% hydrochloric acid was hydrolyzed at room temperature for 40 minutes. The reaction mixture was neutralised by dilute sodium hydroxide solution and extracted with 100 ml of chloroform twice. The chloroform extracts were combined and concentrated in vacuo to a small volume. The concentrate was chromatographed with thin layer chromatography plates (chloroform:methanol, 5:1). The bands containing auramycin C and D were scraped off, extracted with a solvent mixture of chloroform and methanol (4:1) and concentrated in vacuo to dryness to give 12 mg of pure auramycin C and 35 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 bands containing auramycin C and D
  5. extractionextracted with a solvent mixture of chloroform and methanol (4:1)
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-35c37e9a0e374d5ea5924cc8e4911db3
Source dataset
uspto-grants-1983_08
Patent number
US04401812

Reaction notes

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