Hydrochloric Acid → HCID 59003222, compound

HRID 2353868Notes

Reaction equation

HRID 2353868 reaction equation
[OH-:1].[Na+].[CH:3]([O:6][C:7]([N:9]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]([C:32](=[O:34])[CH3:33])[CH2:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)[C:11]2[CH:35]=[C:36](Br)[CH:37]=[CH:38][C:10]1=2)=[O:8])([CH3:5])[CH3:4].Cl.[CH3:41][OH:42]>>[C:32]([N:16]([CH2:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=1)[CH:12]1[CH2:13][CH2:14][CH2:15][N:9]([C:7]([O:6][CH:3]([CH3:5])[CH3:4])=[O:8])[C:10]2[CH:38]=[CH:37][C:36]([C:41]([OH:42])=[O:1])=[CH:35][C:11]1=2)(=[O:34])[CH3:33]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59003133HCID 59003133, compound

Product 1

HCID 59003222HCID 59003222, compoundYield 96%

Procedure

Add 2 N sodium hydroxide solution (2 mL) to a solution of isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.100 g, 0.174 mmol) in methanol (5 mL) at 0° C. and allow to stir for 30 min. Acidify to pH 4 with 2 N hydrochloric acid solution and extract the aqueous mixture with ethyl acetate (3×10 mL). Wash the organic layer with water and brine (10 mL each). Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by triturating with water, to provide the title compound as a white solid (0.091 g, 96%): APCI MS 561 (M+H).

Workup

  1. extractionextract the aqueous mixture with ethyl acetate (3×10 mL)
  2. washWash the organic layer with water and brine (10 mL each)
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure
  6. customPurify the residue
  7. customby triturating with water

Sources & evidence

ORD record
ord-16f8a987321a47bea8fc57e485caaafd
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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