Water → HCID 67437256, compound

HRID 1663242Notes

Reaction equation

HRID 1663242 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)(=[O:22])=[O:21].O>O1CCCC1>[Cl:30][C:25]1[CH:24]=[C:23]([S:20]([N:6]2[CH:5]([CH2:4][C:3]([OH:31])=[O:2])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=3)[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)(=[O:21])=[O:22])[CH:28]=[CH:27][C:26]=1[Cl:29]

Participants

4

Reactant 2

HCID 962WaterHCID 67435854HCID 67435854, compound

Product 1

HCID 67437256HCID 67437256, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [5-(3,4-dichloro-benzenesulfonyl)-8-fluoro-5,6-dihydro-phenanthridin-6-yl]-acetic acid methyl ester (0.48 g, 1 mmol) in a 1:1 mixture of tetrahydrofuran and water (30 mL) lithium hydroxide monohydrate (105 mg, 2.5 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours, then concentrated. The residue was dissolved in a mixture of ethyl acetate (25 mL) and water (25 mL) and acidified with 1N hydrochloride solution. The aqueous phase was separated and extracted with ethyl acetate (2×25 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to yield 0.46 g (98%) of the title compound as white crystals.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in a mixture of ethyl acetate (25 mL) and water (25 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dbb132db67024c9296de3135bb396113
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

Loading…