1,4-Dioxane → HCID 178496744, compound

HRID 1424191Notes

Reaction equation

HRID 1424191 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C@@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:13]([O:15][CH3:16])[CH3:14])=O.O1CCOCC1>CC(O)=O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:9][C:10]([C@@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:13]([O:15][CH3:16])[CH3:14])=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86699104HCID 86699104, compound

Product 1

HCID 178496744HCID 178496744, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of tert-butyl {(1S,2R)-1-[(2-amino-4-bromophenyl)carbamoyl]-2-methoxypropyl}carbamate (Preparation 23, 6.5 g, 16.17 mmol) in AcOH (5 mL) was stirred at room temperature for 3 days followed by 40° C. for 18 hours. The reaction was diluted by the addition of dioxane and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-40% acetonitrile in 0.1% formic acid in water to afford the title compound as a white solid (1.8 g, 29%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified
  3. washeluting with 0-40% acetonitrile in 0.1% formic acid in water

Sources & evidence

ORD record
ord-f3ff5a495add4adfb9c6436ad78c502c
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

Loading…