Sodium Hydroxide → HCID 66934474, compound

HRID 1365619Notes

Reaction equation

HRID 1365619 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][C:6]1[S:7][C:8]([Cl:17])=[C:9]([Cl:16])[C:10]=1[CH2:11][C:12]([O:14]C)=[O:13])C.[OH-].[Na+]>CO>[C:12]([CH2:11][C:10]1[C:9]([Cl:16])=[C:8]([Cl:17])[S:7][C:6]=1[CH2:5][C:4]([OH:18])=[O:3])([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58256105HCID 58256105, compound

Product 1

HCID 66934474HCID 66934474, compoundYield 279.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

A solution of the product from step (c) (1.14 g, 3.66 mmol) in MeOH (7 ml) at 0° C. was treated dropwise with 2M NaOH (3.8 ml). The reaction was warmed to 22° C. and stirred overnight. The solvent was evaporated and the residue was dissolved in 2 M NaOH (50 ml) and extracted with ether (2×50 ml). The basic layer was cooled to 0° C. and acidified to pH 1 with 6 M HCl. The acidic layer was back extracted EtOAc (4×100 ml) and the organic layer was dried (MgSO4) and concentrated. The crude solid was triturated with hexanes and filtered providing 2.75 g (73%) of the subtitle compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 2 M NaOH (50 ml)
  3. extractionextracted with ether (2×50 ml)
  4. temperatureThe basic layer was cooled to 0° C.
  5. dry with materialthe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude solid was triturated with hexanes
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6d536d83451c4b1ea15974a3436fe54e
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

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