N-bromobutanimide → HCID 57684692, compound

HRID 2403732Notes

Reaction equation

HRID 2403732 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-e3baea4eedfd43498f25d4543310c93b
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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