Water → HCID 12136421, compound

HRID 901317Notes

Reaction equation

HRID 901317 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([CH2:15][CH3:16])[C:11]([O:13]C)=[O:12])=[CH:5][C:4]=1[C:17](=[O:36])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[C:31]([F:33])[C:30]([F:34])=[C:29]([F:35])[CH:28]=2)=[CH:22][CH:21]=1.[OH-].[Li+].O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([CH2:15][CH3:16])[C:11]([OH:13])=[O:12])=[CH:5][C:4]=1[C:17](=[O:36])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:28]=[C:29]([F:35])[C:30]([F:34])=[C:31]([F:33])[CH:32]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 12136420HCID 12136420, compound

Product 1

HCID 12136421HCID 12136421, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound (465 mg, 0.927 mmol) of Example 16 in methanol (9 mL) were added 1 mol/L aqueous solution of lithium hydroxide (2.04 mL) and water (3 mL), and the mixture was stirred for 4 hours at room temperature. The reaction mixture was allowed to stand statically for 2 days and then stirred for 18 hours at 50° C. Water was added to the reaction mixture, which was filtered. After the filtrate was cooled to 0° C., it was brought to pH 4 with 3 mol/L hydrochloric acid. The precipitated powder was collected by filtration, dried and submitted to silica gel column chromatography (hexane:ethyl acetate=10:1→2:1) to afford 289 mg of crude powder. This was purified by recrystallization (acetonitrile) to afford 183 mg of white powdery title compound. Yield 40%.

Workup

  1. waitto stand statically for 2 days
  2. stirringstirred for 18 hours at 50° C
  3. filtrationwas filtered
  4. temperatureAfter the filtrate was cooled to 0° C.
  5. filtrationThe precipitated powder was collected by filtration
  6. customdried
  7. customto afford 289 mg of crude powder
  8. customThis was purified by recrystallization (acetonitrile)

Sources & evidence

ORD record
ord-49ec387751f84532b89195fbaec14b6c
Source dataset
uspto-grants-2008_04
Patent number
US07361783B2

Reaction notes

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