Sodium Hydroxide → 3,8-Dihydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

HRID 2419201Notes

Reaction equation

HRID 2419201 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]2[C:11]([N:13]3[CH:17]([OH:18])[CH2:16][CH2:15][CH:14]3[CH:19]=[N:20][C:8]2=[CH:7][C:6]=1[OH:21])=[O:12]>>[CH3:3][O:4][C:5]1[CH:10]=[C:9]2[C:11](=[O:12])[N:13]3[C@@H:14]([CH2:15][CH2:16][C@@H:17]3[OH:18])[CH:19]=[N:20][C:8]2=[CH:7][C:6]=1[OH:21].[CH3:3][O:4][C:5]1[CH:10]=[C:9]2[C:11]([N:13]3[C@H:17]([OH:18])[CH2:16][CH2:15][C@H:14]3[CH:19]=[N:20][C:8]2=[CH:7][C:6]=1[OH:21])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 122745neothramycins

Product 2

HCID 1246863,8-Dihydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-oneHCID 151569Neothramycin A

Procedure

Crystalline methylneothramycin A (225 mg.) obtained in Example 8 was dissolved in 45 ml. of 0.01 NHCl-dioxane (1:1 in volume) and the solution was kept at room temperature (22° C.) for one hour. The solution was adjusted to pH 6.0 with 1 N NaOH and concentrated to dryness under reduced pressure, affording 216 mg. of a colorless powder containing neothramycins A and B. The powder was chromatographed on a column of silica gel (20 g.) by the similar manner as employed in Example 2. Pure neothramycin A (87 mg.) and neothramycin B (69 mg.) were obtained.

Workup

  1. customCrystalline methylneothramycin A (225 mg.) obtained in Example 8
  2. dissolutionwas dissolved in 45 ml
  3. customwas kept at room temperature
  4. custom(22° C.)
  5. customfor one hour
  6. concentrationconcentrated to dryness under reduced pressure
  7. customaffording 216 mg
  8. customThe powder was chromatographed on a column of silica gel (20 g.) by the similar manner

Sources & evidence

ORD record
ord-1bb930e7317e4bb4b43642449c6a5d1b
Source dataset
uspto-grants-1978_08
Patent number
US04105658

Reaction notes

Loading…