Potassium Carbonate → HCID 86586419, compound

HRID 1266589Notes

Reaction equation

HRID 1266589 reaction equation
[CH3:1][O:2][C:3](=[O:41])[C@H:4]([NH:27][S:28]([C:31]1[CH:40]=[CH:39][C:34]2[N:35]=[C:36](Cl)[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.C([O-])([O-])=O.[K+].[K+].O.[CH2:49]([O:51][C:52](=O)[CH3:53])C>CC#N>[CH3:1][O:2][C:3](=[O:41])[C@H:4]([NH:27][S:28]([C:31]1[CH:40]=[CH:39][C:34]2[N:35]=[C:36]([S:28][C:31]3[CH:40]=[CH:53][C:52]([O:51][CH3:49])=[CH:33][CH:32]=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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22728543Water ethylacetateHCID 86586420HCID 86586420, compound

Product 1

HCID 86586419HCID 86586419, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2R)-2-[(2-Chlorobenzthiazol-6-sulfonyl)amino]-3-(4-(3-phthalimido-1-propyl)oxyphenyl)propionic acid methylester (0.24 g, 0.39 mmol) prepared in a similar manner as in Example 59 was dissolved in MeCN (3 mL). K2CO3 (0.081 g, 1.5 equi.) were added to the solution in a solid form and then, 4-methoxybenzthiol (0.053 mL, 1.1 equi.) was added and refluxed for 3 hours. After starting material was exhausted, water/ethylacetate (5 mL/10 mL) was added and the product was extracted with an organic solvent. The organic phase was washed with NaCl solution, dried over anhydrous MgSO4, distilled under reduced pressure and then, purified on silica gel chromatography using ethylacetate/n-hexane (1/2) to prepare the titled compound, (2R)-2-[(2-(4-methoxyphenylthio)benzthiazol-6-sulfonyl)amino]-3-(4-(3-phthalimido-1-propyl)oxyphenyl)propionic acid methylester (0.2 g, 70%).

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionthe product was extracted with an organic solvent
  3. washThe organic phase was washed with NaCl solution
  4. dry with materialdried over anhydrous MgSO4
  5. distillationdistilled under reduced pressure
  6. custompurified on silica gel chromatography
  7. customto prepare the titled compound, (2R)-2-[(2-(4-methoxyphenylthio)benzthiazol-6-sulfonyl)amino]-3-(4-(3-phthalimido-1-propyl)oxyphenyl)propionic acid methylester (0.2 g, 70%)

Sources & evidence

ORD record
ord-bdc5106213274a15996c5062d68c1875
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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