Anisomycin → Deacetylanisomycin

HRID 1755450Notes

Reaction equation

HRID 1755450 reaction equation
C([O:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][NH:7][C@@H:6]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=O)C.N.CO>>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][C@@H:6]2[C@H:5]([OH:4])[C@@H:9]([OH:10])[CH2:8][NH:7]2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 253602AnisomycinHCID 21705897Ammonia methanol

Product 1

HCID 11790817Deacetylanisomycin

Procedure

To a 500 mL round bottom flask containing solid (2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate (513.3 mg, 1.935 mmol) and a magnetic stir bar is added 2M NH3/MeOH (200 mL, 400 mmol). The resulting light tan solution is capped and stirred at room temp for 5 days. The solvent is removed in vacuo to give the title compound that is used directly “as is” in the next step. LC/MS (Condition A): ret. T=1.42 min, (M+H)+ 224.11.

Workup

  1. customThe resulting light tan solution is capped
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-785f9845e5f84015877756ae03d66b59
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

Loading…