Thiophenol → HCID 86586417, compound

HRID 1266582Notes

Reaction equation

HRID 1266582 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@H:4]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:15]2[N:16]=[C:17](Cl)[S:18][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].C([O-])([O-])=O.[K+].[K+].[C:29]1([SH:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O.C(OC(=O)C)C>CC#N>[CH3:1][O:2][C:3](=[O:22])[C@H:4]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:15]2[N:16]=[C:17]([S:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[S:18][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 22728543Water ethylacetateHCID 86586416HCID 86586416, compound

Product 1

HCID 86586417HCID 86586417, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2R)-3-methyl-2-[(2-chlorobenzthiazol-6-sulfonyl)amino]butanoic acid methylester (0.154 mg, 0.44 mmol) prepared in a similar manner as in Example 20 was dissolved in MeCN (3 mL) and added solid K2CO3 (0.1 mg, 1.6 equi.). Thiophenol (0.055 mL, 1.2 equi.) was also added and the reaction solution was refluxed for 3 hours. When starting material was disappeared, H2O/ethylacetate (5 mL/10 mL) was added for extraction of product. The extracted product in organic phase was washed with NaCl solution, dried over MgSO4 and distilled under reduced pressure. The extracted product was crystallized with n-hexane/ethylacetate (3/1) solution to prepare the titled compound, (2R)-3-methyl-2-[(2-phenylthiobenzthiazol-6-sulfonyl)amino]butanoic acid methylester (190 mg, 99%).

Workup

  1. temperaturethe reaction solution was refluxed for 3 hours
  2. washThe extracted product in organic phase was washed with NaCl solution
  3. dry with materialdried over MgSO4
  4. distillationdistilled under reduced pressure
  5. customThe extracted product was crystallized with n-hexane/ethylacetate (3/1) solution
  6. customto prepare the titled compound, (2R)-3-methyl-2-[(2-phenylthiobenzthiazol-6-sulfonyl)amino]butanoic acid methylester (190 mg, 99%)

Sources & evidence

ORD record
ord-84dfe1a54df0478d8bdbaa89e8efd643
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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