Lithium Hydroxide → HCID 69555262, compound

HRID 1266579Notes

Reaction equation

HRID 1266579 reaction equation
C[O:2][C:3](=[O:25])[C@H:4]([NH:8][S:9]([C:12]1[CH:24]=[CH:23][C:15]2[N:16]=[C:17]([S:19][CH2:20][CH2:21][CH3:22])S[C:14]=2[CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-:27]>C1COCC1.O>[CH3:6][CH:5]([CH3:7])[C@@H:4]([NH:8][S:9]([C:12]1[CH:24]=[CH:23][C:15]2[N:16]=[C:17]([S:19][CH2:20][CH2:21][CH3:22])[O:27][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[C:3]([OH:2])=[O:25]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86586414HCID 86586414, compound

Product 1

HCID 69555262HCID 69555262, compound

Reagents, catalysts & solvents 1

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

Procedure

(2R)-3-methyl-2-[(2-propylthiobenzthiazol-6-sulfonyl)amino]butanoic acid methylester (0.19 g, 0.48 mmol) was dissolved in THF/H2O (2 mL/2 mL), and LiOH (0.10 g, 5 equi.) was added. After reflux for 6 hours, the reaction 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-propylthiobenzoxazol-6-sulfonyl)amino]butanoic acid (0.14 g, 77%).

Workup

  1. temperatureAfter reflux for 6 hours
  2. distillationthe reaction 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-propylthiobenzoxazol-6-sulfonyl)amino]butanoic acid (0.14 g, 77%)

Sources & evidence

ORD record
ord-5d1b72c29b304085a81c0f381fdff7a2
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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