Triethylamine → HCID 86586413, compound

HRID 1266578Notes

Reaction equation

HRID 1266578 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].C(N(CC)CC)C.[CH2:18]([S:21][C:22]1[O:23][C:24]2[CH:30]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:27][C:25]=2[N:26]=1)[CH2:19][CH3:20]>ClCCl>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([NH:6][S:31]([C:29]1[CH:28]=[CH:27][C:25]2[N:26]=[C:22]([S:21][CH2:18][CH2:19][CH3:20])[O:23][C:24]=2[CH:30]=1)(=[O:32])=[O:33])[CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11984198Methyl D-valinate hydrochlorideHCID 18551583HCID 18551583, compound

Product 1

HCID 86586413HCID 86586413, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

(D)-valine methylester hydrochloride (0.2 g, 1.19 mmol) was dispersed in dichloromethane (3 mL) and cooled down to 0° C., and triethylamine (0.37 mL, 3 equi.) was added. The dichloromethane solution containing 2-n-propylthiobenzoxazol-6-sulfonyl chloride (0.26 g, 1.0 equi.) prepared in the above Example and dichloromethane (2 mL) was also 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, distilled under reduced pressure and dried under vacuum, to give (2R)-3-methyl-2-[(2-propylthiobenzoxazol-6-sulfonyl)amino] butanoic acid methylester(0.31 g, 67%).

Workup

  1. additionwas also added
  2. temperaturewhile maintaining the temperature of 0° C
  3. washthe organic phase was washed with 1N HCl
  4. dry with materialdried over MgSO4
  5. distillationdistilled under reduced pressure
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4148f8f4ba9f42a7b32257b3a20880b1
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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