Hydrochloric Acid → HCID 10113257, compound

HRID 489579Notes

Reaction equation

HRID 489579 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:33])[C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=4)=[C:22]([CH3:32])[CH:21]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[OH-:36].[Na+].Cl>CC(C)=O>[C:26]1([C:23]2[CH:24]=[CH:25][C:20]([C:19]([N:10]3[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13][N:14]4[C:5]([C:3]([OH:36])=[O:4])=[CH:6][CH:7]=[C:8]4[CH2:9]3)=[O:33])=[CH:21][C:22]=2[CH3:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 102799352,2,2-Trichloro-1-[10-(4-cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanone

Product 1

HCID 10113257HCID 10113257, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.2.2-Trichioro-1-[10-(4-cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pvrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanone of Step D (0.700 g, 1.33 mmol), was dissolved in acetone (8.9 mL) followed by addition of 2.5 N sodium hydroxide (1.60 mL, 3.99 mmol). The reaction was stirred at room temperature for 3 hours, and acidified with 2 N hydrochloric acid. The acidic mixture was extracted with diethyl ether and the organic phase extracted with 1 N sodium hydroxide. The combined basic extracts were acidified with 2 N hydrochloric acid, and extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was recrystallized from diethyl ether to afford 0.450 g of the title compound as white crystals, 193° C. (dec.)

Workup

  1. extractionThe acidic mixture was extracted with diethyl ether
  2. extractionthe organic phase extracted with 1 N sodium hydroxide
  3. extractionextracted with diethyl ether
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-e4ca7824af7f40dabee3eb02db9eadde
Source dataset
uspto-grants-2005_12
Patent number
US06977254B2

Reaction notes

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