Triethylamine → Methyl 3-hydroxy-2-[4-(4-pyridinyloxy)-benzenesulfonylamino]propionate

HRID 1420629Notes

Reaction equation

HRID 1420629 reaction equation
Cl.[NH2:2][C@H:3]([C:6]([O:8][CH3:9])=[O:7])[CH2:4][OH:5].C(N(CC)CC)C.[N:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1>C(Cl)Cl>[OH:5][CH2:4][CH:3]([NH:2][S:30]([C:27]1[CH:26]=[CH:25][C:24]([O:23][C:20]2[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=2)=[CH:29][CH:28]=1)(=[O:31])=[O:32])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27352584-(4-Pyridyloxy)benzenesulfonyl chloride

Product 1

HCID 18782087Methyl 3-hydroxy-2-[4-(4-pyridinyloxy)-benzenesulfonylamino]propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled mixture of 6.84 g (44 mmol) of D, L-serine, methyl ester hydrochloride and 21.4 (144 mmol) of triethylamine in 90 ml of CH2Cl2 was added a solution of 10.78 g (40 mmol) of 4-(4-pyridinyloxy)benzenesulfonyl chloride in 50 ml of CH2Cl2. The mixture was stirred at room temperature overnight, diluted with 50 ml of CH2Cl2 and the solution washed with H2O, 1N NaHCO3, 2N citric acid, brine and dried (with Na2SO4). The solvent was removed under vacuum to give a solid. The aqueous 2N citric acid wash was made basic with saturated NaHCO3 and then extracted with CH2Cl2. The solvent was removed to give a solid. The two crops of solid were combined, washed with H2O and then hexane. The solid was dried at 80° C. to give 10.95 g of methyl 3-hydroxy-2-[4-(4-pyridinyloxy)-benzenesulfonylamino]propionate as white crystals, mp. 137-139° C.

Workup

  1. washthe solution washed with H2O, 1N NaHCO3, 2N citric acid, brine
  2. dry with materialdried (with Na2SO4)
  3. customThe solvent was removed under vacuum
  4. customto give a solid
  5. washThe aqueous 2N citric acid wash
  6. extractionextracted with CH2Cl2
  7. customThe solvent was removed
  8. customto give a solid
  9. washwashed with H2O
  10. customThe solid was dried at 80° C.

Sources & evidence

ORD record
ord-bb8c0c94f4924320aba3f6cb50d6c36c
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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