N-bromobutanimide → HCID 57684692, compound

HRID 425053Notes

Reaction equation

HRID 425053 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:35])=[CH2:34])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2].C1C(=O)N([Br:48])C(=O)C1>ClC1C=CC=CC=1>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:33]([CH2:35][Br:48])=[CH2:34])=[CH:31][CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57684693HCID 57684693, compound

Product 1

HCID 57684692HCID 57684692, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl) benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (intermediate AZ) (236 mg, 0.412 mmol) and NBS (110 mg, 0.618 mmol) in chlorobenzene (5 mL) was stirred at 135° C. for 2 h. The solids were filtered and washed with AcOEt. The organic portion was washed 1× with H2O and 1× with brine prior to drying over Na2SO4. Concentration and purification of the resulting residue by preparative TLC gave intermediate AZ (144 mg).

Workup

  1. filtrationThe solids were filtered
  2. washwashed with AcOEt
  3. washThe organic portion was washed 1× with H2O and 1× with brine
  4. dry with materialto drying over Na2SO4
  5. concentrationConcentration and purification of the resulting residue by preparative TLC
  6. customgave intermediate AZ (144 mg)

Sources & evidence

ORD record
ord-6c61171ae130434db439a7fed9017977
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

Loading…