Lithium Hydroxide → 4-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}-benzoic acid

HRID 1517168Notes

Reaction equation

HRID 1517168 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:24]([CH3:26])[CH3:25])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:6][CH:5]=1.[Li+].[OH-]>O1CCCC1>[C:30]([O:29][C:27]([CH:23]([N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:34])=[O:2])=[CH:9][CH:8]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:24]([CH3:26])[CH3:25])=[O:28])([CH3:32])([CH3:33])[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 694513514-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}benzoic acid methyl ester

Product 1

HCID 694468364-{[(1-tert-Butoxycarbonyl-2-methyl-propyl)-(4-methoxy-benzenesulfonyl)-amino]-methyl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The diester (Compound 7*) (151 mg, 0.31 mmol) was dissolved in tetrahydrofuran (2 ml) and 4N LiOH (250 μl) was added at ambient temperature. The mixture was heated to 60° C. for 5 hours when HPLC monitoring showed the hydrolysis was completed. The mixture was cooled to ambient temperature and the solvent was evaporated. The residue was dissolved in water and the clear solution extracted with once with diethyl ether. Then the aqueous phase was cooled to 5° C. (ice/water) and neutralised with 1N HCl and after which it was extracted with ethyl acetate (3×5 ml). The combined ethyl acetate phases was extracted with water (5 ml) and brine (5 ml), dried with (Na2SO4), filtered and evaporated to afford the product as white foam. Yield 133 mg (90%).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionthe clear solution extracted with once with diethyl ether
  5. temperatureThen the aqueous phase was cooled to 5° C. (ice/water)
  6. extractionafter which it was extracted with ethyl acetate (3×5 ml)
  7. extractionThe combined ethyl acetate phases was extracted with water (5 ml) and brine (5 ml)
  8. dry with materialdried with (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-7f122147ac71481a9ff85223b417ae98
Source dataset
uspto-grants-2012_07
Patent number
US08231858B2

Reaction notes

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