Triethylamine → HCID 86586416, compound

HRID 1266581Notes

Reaction equation

HRID 1266581 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[Cl:11][C:12]1[S:13][C:14]2[CH:20]=[C:19]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:17][C:15]=2[N:16]=1.C(N(CC)CC)C>ClCCl>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([NH:6][S:21]([C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([Cl:11])[S:13][C:14]=2[CH:20]=1)(=[O:22])=[O:23])[CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11984198Methyl D-valinate hydrochlorideHCID 123508702-Chloro-1,3-benzothiazole-6-sulfonyl chloride

Product 1

HCID 86586416HCID 86586416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

(D)-valine methylester hydrochloride (0.33 g, 2.0 mmol) was dispersed in dichloromethane (5 mL) and cooled down to 0° C. 2-Chloro-6-benzthiazolsulfonyl chloride (0.5 g, 1.0 equi.) prepared in Example 13 was dissolved in dichloromethane (3 mL) to give a dichloromethane solution. Triethylamine (0.83 mL, 3 equi.) and the dichloromethane solution were added while maintaining the temperature of 0° C. When starting material was exhausted after 5 hours, the organic phase was washed with 1N HCl, dried over MgSO4 and distilled under reduced pressure. Then, the product was eluted and purified on silica gel chromatography using ethylacetate/n-hexane (1/3) solvent to prepare the titled compound, (2R)-3-methyl-2-[(2-chlorobenzthiazol-6-sulfonyl)amino] butanoic acid methylester (0.65 g, 90%).

Workup

  1. temperaturewhile maintaining the temperature of 0° C
  2. washthe organic phase was washed with 1N HCl
  3. dry with materialdried over MgSO4
  4. distillationdistilled under reduced pressure
  5. washThen, the product was eluted
  6. custompurified on silica gel chromatography
  7. customto prepare the titled compound, (2R)-3-methyl-2-[(2-chlorobenzthiazol-6-sulfonyl)amino] butanoic acid methylester (0.65 g, 90%)

Sources & evidence

ORD record
ord-2fcb8cf0301d44f685c8860be91a6c97
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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