Sodium Hydroxide → HCID 178455655, compound

HRID 2249970Notes

Reaction equation

HRID 2249970 reaction equation
[OH-].[Na+].[CH3:3][C:4]([S:7]([NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19]C)=[O:18])[CH2:13][CH2:12]1)(=[O:9])=[O:8])([CH3:6])[CH3:5]>CO>[CH3:6][C:4]([S:7]([NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)(=[O:8])=[O:9])([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501252HCID 178501252, compound

Product 1

HCID 178455655HCID 178455655, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
24 °C

Procedure

An aqueous solution (4.4 L) of sodium hydroxide (441 g, 2.5 eq) was added dropwise to a solution of methyl trans-4-(2-methylpropane-2-sulfonylamino)cyclohexane carboxylate (12) (1222 g, 4,407 mol) in methanol (2.45 L) over 30 minutes at 4 to 12° C. The mixture was stirred for an hour at 12 to 36° C. and methanol was removed under reduced pressure. The pH value of the residue was adjusted to 9.7 with hydrochloric acid and the mixture was washed with ethyl acetate (4.5 L). The organic layer was extracted with water (1 L). Aqueous layers were combined, acidified with hydrochloric acid, and extracted with ethyl acetate (5 L, 4 L). Each of organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The appeared crystals were collected by filtration and washed with IPE to obtain (13) (1012 g, 87.2%).

Workup

  1. custommethanol was removed under reduced pressure
  2. washthe mixture was washed with ethyl acetate (4.5 L)
  3. extractionThe organic layer was extracted with water (1 L)
  4. extractionextracted with ethyl acetate (5 L, 4 L)
  5. washEach of organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe appeared crystals were collected by filtration
  9. washwashed with IPE

Sources & evidence

ORD record
ord-e1340a54a1754df481839d616bdf8f26
Source dataset
uspto-grants-2008_01
Patent number
US07314950B2

Reaction notes

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