Hydrochloric Acid → HCID 86624380, compound

HRID 508065Notes

Reaction equation

HRID 508065 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:5]=[C:4]([CH3:18])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])=[C:29]([F:40])[CH:28]=2)[CH:20]=1.CO.[OH-].[Na+].Cl.[C:46]1([S:52]([OH:55])(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(OCC)(=O)C.O1CCCC1>[C:46]1([S:52]([OH:55])(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[CH3:18][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:29]([F:40])[CH:28]=2)[CH:20]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7371Benzenesulfonic AcidHCID 14798Sodium HydroxideHCID 23157691HCID 23157691, compound

Product 1

HCID 86624380HCID 86624380, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of ethyl 3-{4-[({2′,6′-dimethyl-4′-[3-(2-oxopyrrolidin-1-yl)propoxy]biphenyl-3-yl}methyl)amino]-2-fluorophenyl}propanoate (1.13 g, 2.07 mmol), methanol (5 mL) and tetrahydrofuran (10 mL) was added 1 M aqueous sodium hydroxide solution (4.14 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with 1M hydrochloric acid, and diluted with ethyl acetate, and the organic layer was washed with saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/2) to give a colorless oil. The obtained oil was diluted with ethyl acetate, and benzenesulfonic acid was added. The precipitated crystals were collected by filtration, washed, and dried to give the title compound (0.78 g, yield 56%) as colorless crystals.

Workup

  1. washthe organic layer was washed with saturated brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/2)
  5. customto give a colorless oil
  6. additionwas added
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-3f4ec84d19f243be821d7cc20d38d471
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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