Hydrogen Bromide → HCID 178476734, compound

HRID 1786280Notes

Reaction equation

HRID 1786280 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:11][C@H:10]([O:12][C:13]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]3[C:14]=2[C:15]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[NH:16][C:17](=[O:24])[NH:18]3)[CH2:9]1)=[O:7])(C)(C)C.Br.O>C(O)(=O)C>[C:6]([OH:7])(=[O:5])[CH3:8].[Cl:23][C:20]1[CH:21]=[CH:22][C:13]([O:12][C@H:10]2[CH2:9][C@H:8]([C:6]([OH:7])=[O:5])[CH2:11]2)=[C:14]2[C:19]=1[NH:18][C:17](=[O:24])[NH:16][C:15]12[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 178451178HCID 178451178, compound

Product 1

HCID 178476734HCID 178476734, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The product of step (a) (207 g, 0.492 mol) was slurried in acetic acid (3100 ml) and heated to 60° C. 48% Hydrobromic acid (4.93 mol) was added dropwise keeping the temperature at 60° C. The solution was stirred at 60° C. for 30 minutes. Water (700 ml) was added dropwise keeping the temperature above 55° C. The slurry was cooled to 20° C. and stirred for a further 30 minutes after which it was filtered, washed with acetic acid:water (2000 ml) and water (1000 ml) before being dried in a vacuum oven overnight at 60° C. to yield a white solid of the title compound as an acetic acid solvate (153.6 g, 73.5%).

Workup

  1. customat 60° C
  2. customthe temperature above 55° C
  3. temperatureThe slurry was cooled to 20° C.
  4. stirringstirred for a further 30 minutes after which it
  5. filtrationwas filtered
  6. washwashed with acetic acid
  7. dry with materialwater (2000 ml) and water (1000 ml) before being dried in a vacuum oven overnight at 60° C.

Sources & evidence

ORD record
ord-519cad054db84e83af78a0efbeb0aa4f
Source dataset
uspto-grants-2009_03
Patent number
US07507742B2

Reaction notes

Loading…