Lithium Hydroxide → HCID 10269917, compound

HRID 1266576Notes

Reaction equation

HRID 1266576 reaction equation
C[O:2][C:3](=[O:23])[C@H:4]([NH:8][S:9]([C:12]1[CH:22]=[CH:21][C:15]2[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-]>C1COCC1.O>[CH3:6][CH:5]([CH3:7])[C@@H:4]([NH:8][S:9]([C:12]1[CH:22]=[CH:21][C:15]2[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[C:3]([OH:23])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86586411HCID 86586411, compound

Product 1

HCID 10269917HCID 10269917, compound

Reagents, catalysts & solvents 1

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

Procedure

(2R)-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl)amino]butanoic acid methylester (0.35 g, 0.9 mmol) was dissolved in THF/H2O (2 mL/2 mL), and added LiOH (0.16 g, 5 equi.). After the reaction soluton was refluxed for 6 hours, the solution was distilled under reduced pressure and treated with 1N HCl. The product was extracted with ethylacetate (10 mL). The separated organic phase was washed with NaCl solution, dried over MgSO4, distilled under reduced pressure and dried under vacuum, to prepare the titled compound, (2R)-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl)amino]butanoic acid (54 mg, 23%).

Workup

  1. temperatureAfter the reaction soluton was refluxed for 6 hours
  2. distillationthe solution was distilled under reduced pressure
  3. additiontreated with 1N HCl
  4. extractionThe product was extracted with ethylacetate (10 mL)
  5. washThe separated organic phase was washed with NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationdistilled under reduced pressure
  8. customdried under vacuum
  9. customto prepare the titled compound, (2R)-3-methyl-2-[(2-methylthiobenzthiazol-6-sulfonyl)amino]butanoic acid (54 mg, 23%)

Sources & evidence

ORD record
ord-3ed936e1646e416fa67d53fcf877f2d0
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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