Lithium Hydroxide → HCID 20577788, compound

HRID 1266590Notes

Reaction equation

HRID 1266590 reaction equation
C[O:2][C:3](=[O:49])[C@H:4]([NH:27][S:28]([C:31]1[CH:48]=[CH:47][C:34]2[N:35]=[C:36]([S:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[S:37][C:33]=2[CH:32]=1)(=[O:30])=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])=[CH:8][CH:7]=1.[Li+].[OH-]>C1COCC1.O>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([S:38][C:36]2[S:37][C:33]3[CH:32]=[C:31]([S:28]([NH:27][C@H:4]([CH2:5][C:6]4[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]5[C:20](=[O:21])[C:19]6=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]6[C:17]5=[O:26])=[CH:8][CH:7]=4)[C:3]([OH:49])=[O:2])(=[O:29])=[O:30])[CH:48]=[CH:47][C:34]=3[N:35]=2)=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86586419HCID 86586419, compound

Product 1

HCID 20577788HCID 20577788, compound

Reagents, catalysts & solvents 1

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

Procedure

(2R)-2-[(2-(4-Methoxyphenylthio)benzthiazol-6-sulfonyl)amino]-3-(4-(3-phthalimido-1-propyl)oxyphenyl) propionic acid methylester (0.196 g, 0.27 mmol) prepared in Example 61 was dissolved in THF/H2O (2 mL/2 mL), and LiOH(0.057 g, 5 equi.) was added and refluxed for 12 hours. Then, the reaction solution was distilled under reduced pressure to remove the solvent and treated with 1N HCl. The product was extracted with ethylacetate (10 mL). The separated organic phase was washed with NaCl solution, dried over anhydrous MgSO4, distilled under reduced pressure and dried under vacuum to prepare the titled compound, (2R)-2-[(2-(4-methoxyphenylthio)benzthiazol-6-sulfonyl)amino]-3-(4-(3-phthalimido-1-propyl)oxyphenyl) propionic acid (0.15 g, 80%).

Workup

  1. temperaturerefluxed for 12 hours
  2. distillationThen, the reaction solution was distilled under reduced pressure
  3. customto remove the solvent
  4. additiontreated with 1N HCl
  5. extractionThe product was extracted with ethylacetate (10 mL)
  6. washThe separated organic phase was washed with NaCl solution
  7. dry with materialdried over anhydrous MgSO4
  8. distillationdistilled under reduced pressure
  9. customdried under vacuum
  10. customto prepare the titled compound, (2R)-2-[(2-(4-methoxyphenylthio)benzthiazol-6-sulfonyl)amino]-3-(4-(3-phthalimido-1-propyl)oxyphenyl) propionic acid (0.15 g, 80%)

Sources & evidence

ORD record
ord-cae1e4dde28f49d4b651927e737f0c56
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

Loading…