4-Methoxybenzenesulfonyl chloride → N-(4-Methoxybenzenesulfonyl)-L-serine, t-butyl ester

HRID 1420581Notes

Reaction equation

[NH2:1][C@H:2]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:1][C@H:2]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][OH:4])(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 12.18 g (0.0756 mol) of L-serine, t-butyl ester, 26.52 ml of triethylamine in 160 ml of CH2Cl2 (cooled in an ice bath) was added, in small portions, 16.1 g (0.0771 mol) of 4-methoxybenzene-sulfonyl chloride. The mixture was stirred at 0° C. for 0.5 hours and at room temperature overnight. The mixture was washed with H2O, 2N citric acid, brine and dried with Na2SO4. The solvent was removed under vacuum to give 25.34 g of solid which was triturated with hexane. The solid was recrystallized from 120 ml of toluene to give 12.18 g (48.7%) of product as a white solid. The filtrate was concentrated and the residue chromatographed on silica gel with hexane-ethyl acetate (7:3) as eluent to give 5.71 g (22.8%) of white solid. m.p. 70-75° C. Anal. for C14H21NO6S: Calc'd: C. 50.7; H,6.4; N,4.2; Found: C, 50.4; H,6.3; N,4.4.

Workup

washThe mixture was washed with H2O, 2N citric acid, brine
dry with materialdried with Na2SO4
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-a6b12dfa2b974068ae660be3e4a62c74
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071903

Reaction notes

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