Acetone → HCID 69313753, compound

HRID 2053749Notes

Reaction equation

HRID 2053749 reaction equation
ClC(Cl)(Cl)C(C1[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][C:27]=4[CH3:32])=[CH:22][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.[OH-:36].[Na+].Cl.C[C:40]([CH3:42])=[O:41]>>[CH3:32][C:27]1[CH2:28][CH2:29][CH2:30][CH2:31][C:26]=1[C:23]1[CH:22]=[CH:21][C:20]([C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:42]([C:40]([OH:36])=[O:41])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:33])=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69314912HCID 69314912, compound

Product 1

HCID 69313753HCID 69313753, compoundYield 97%

Procedure

2,2,2-Trichloro-1-{10-[4-(2-methyl-cyclohex-1-en-1-yl)-benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}-ethanone of Step E (1 g, 1.67 mmol) was dissolved in acetone (11.1 mL) followed by the addition of 2.5 N aqueous sodium hydroxide (1.2 mL, 3.01 mmol). After stirring at room temperature for six hours, the reaction mixture was neutralized with 2 N hydrochloric acid and extracted with diethyl ether. The organic phase was extracted with 1 N sodium hydroxide, the combined basic extracts were acidified with 2 N hydrochloric acid and extracted with diethyl ether. The combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by HPLC (Primesphere 5 C-18, solvent gradient of 65 to 90% acetonitrile in 1% aqueous trifluoroacetic acid) to afford (97%) the title compound (0.805 g) as a white solid. m.p. 171° C.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe organic phase was extracted with 1 N sodium hydroxide
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by HPLC (Primesphere 5 C-18, solvent gradient of 65 to 90% acetonitrile in 1% aqueous trifluoroacetic acid)

Sources & evidence

ORD record
ord-f76afc4548cd41b69c6569072a115d2c
Source dataset
uspto-grants-2008_02
Patent number
US07326700B2

Reaction notes

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