Lithium Hydroxide → HCID 69554660, compound

HRID 1266584Notes

Reaction equation

HRID 1266584 reaction equation
C[O:2][C:3](=[O:31])[C@H:4]([N:8]([S:16]([C:19]1[CH:30]=[CH:29][C:22]2[N:23]=[C:24]([S:26][CH2:27][CH3:28])[S:25][C:21]=2[CH:20]=1)(=[O:18])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:5]([CH3:7])[CH3:6].[Li+].[OH-]>C1COCC1.O>[CH3:7][CH:5]([CH3:6])[C@@H:4]([N:8]([S:16]([C:19]1[CH:30]=[CH:29][C:22]2[N:23]=[C:24]([S:26][CH2:27][CH3:28])[S:25][C:21]=2[CH:20]=1)(=[O:17])=[O:18])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:3]([OH:31])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 91357348HCID 91357348, compound

Product 1

HCID 69554660HCID 69554660, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

(2R)-3-methyl-2-[(ethylthio-6-benzthiazolsulfonyl) benzylamino]butanoic acid methylester (180 mg, 0.376 mmol) prepared in Example 26 was dissolved in THF/H2O (2 mL/2 mL), and LiOH (0.08 g, 5 equi.) was added. After reflux for 6 days, the reaction solution was distilled under reduced pressure and treated with 1N HCl, and ethylacetate (10 mL) was added to extract the product. The separated organic phase containing product was washed with NaCl solution, dried over MgSO4 and distilled under reduced pressure. The remaining material was purified on silica gel chromatography using ethylacetate/n-hexane (1/1) and ethylacetate/dichloromethane/acetate (1/1/trace amount) as solvent and dried under vacuum to prepare the titled compound, (2R)-3-methyl-2-[(ethylthio-6-benzthiazolsulfonyl)benzylamino]butanoic acid (0.1 g, 57%).

Workup

  1. temperatureAfter reflux for 6 days
  2. distillationthe reaction solution was distilled under reduced pressure
  3. additiontreated with 1N HCl, and ethylacetate (10 mL)
  4. additionwas added
  5. extractionto extract the product
  6. additionThe separated organic phase containing product
  7. washwas washed with NaCl solution
  8. dry with materialdried over MgSO4
  9. distillationdistilled under reduced pressure
  10. customThe remaining material was purified on silica gel chromatography
  11. customdried under vacuum
  12. customto prepare the titled compound, (2R)-3-methyl-2-[(ethylthio-6-benzthiazolsulfonyl)benzylamino]butanoic acid (0.1 g, 57%)

Sources & evidence

ORD record
ord-73dba95e2050410e9a226f4cf3167135
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

Loading…