Lithium Hydroxide → HCID 10184927, compound

HRID 857429Notes

Reaction equation

HRID 857429 reaction equation
C([O:3][C:4](=[O:30])[C:5]([CH:8]1[C:12]2=[C:13]([S:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:14]3[C:15]([Br:21])=[CH:16][C:17]([F:20])=[CH:18][C:19]=3[N:11]2[CH2:10][CH2:9]1)([F:7])[F:6])C.[Li+].[OH-]>O1CCOCC1>[Br:21][C:15]1[C:14]2[C:13]([S:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[C:12]3[CH:8]([C:5]([F:6])([F:7])[C:4]([OH:30])=[O:3])[CH2:9][CH2:10][N:11]3[C:19]=2[CH:18]=[C:17]([F:20])[CH:16]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 91557434HCID 91557434, compound

Product 1

HCID 10184927HCID 10184927, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The ethyl ester (65 mg) from Step 1 was dissolved in 2 mL of old (peroxide containing) 1,4-dioxane. 1 N LiOH was added (0.25 mL) and the mixture was stirred at room temperature for 2 h. Excess 1 N NaH2PO4 was added and the mixture was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel chromatography on preparative plates eluting with 25% EtOH/CH2CL2+3% AcOH gave the desired compound (32 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography on preparative plates
  6. washeluting with 25% EtOH/CH2CL2+3% AcOH

Sources & evidence

ORD record
ord-b57e03fbfe5143d4b04755025e423ad6
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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