4-Methoxybenzenesulfonyl chloride → Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

HRID 1420589Notes

Reaction equation

[NH2:1][CH:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[OH:4][CH2:3][CH:2]([NH:1][S:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:23][CH:22]=1)(=[O:26])=[O:25])[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 5.0 g (32.14 mmol) of D,L-serine, methyl ester and 15.7 ml (0.012 mol) of triethylamine in 100 ml of CH2Cl2, cooled to 0° C., was added portionwise 6.64 g (32.14 mmol) of 4-methoxybenzenesulfonyl chloride. The mixture was then stirred under argon at room temperature for 2 days. The mixture was diluted with 100 ml of CH2Cl2 and then washed with 60 ml each of H2O, 2 N citric acid, brine and dried with Na2SO4. The solvent was removed under vacuum to give a solid. Crystallization from ethyl acetate gave 5.0 g (54%) of white crystals, m.p. 92-94° C. Anal. for C11H15NO6S: Calc'd: C,45.7; H,5.2; N,4.8; S,11.1; Found: C,45.6; H,5.2; N,4.8; S,1.11.

Workup

washwashed with 60 ml each of H2O, 2 N citric acid, brine
dry with materialdried with Na2SO4
customThe solvent was removed under vacuum
customto give a solid
customCrystallization from ethyl acetate

Sources & evidence

ORD record: ord-ff55a62cd32540b39d573dfcfb2d1b66
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071903

Reaction notes

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