Triethylamine → HCID 57280269, compound

HRID 2414673Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[S:6][CH2:5][NH:4][CH:3]1[C:7]([OH:9])=[O:8].C(N(CC)CC)C.[C:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)#[C:19][CH2:20][CH3:21]>O1CCOCC1.O.C(OCC)(=O)C>[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:4]2[C@@H:3]([C:7]([OH:9])=[O:8])[C:2]([CH3:10])([CH3:1])[S:6][CH2:5]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a room temperature solution of 4.3 g (32.3 mmol) of 5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (J. Med. Chem. 1989, 32(2), 466-472.) in 30 ml of dioxane:water (2:1) containing 4.9 mL (35.5 mmol) of triethylamine was added 7.9 g (32.3 mmol) of 4-butynyloxybenzenesulfonyl chloride. The mixture was stirred at 25° C. for 18 h. The resulting mixture was diluted with ethyl acetate and washed with 1N aqueous hydrochloric acid (3×). The organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo to afford a foam which was chromatographed on silica gel eluting with methanol/dichloromethane to give (4S)-3-{[4-(2- butynyloxy)phenyl]sulfonyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid as a white solid. Electrospray Mass Spec 368.1 (M−H)−

Workup

washwashed with 1N aqueous hydrochloric acid (3×)
dry with materialThe organic phase was dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto afford a foam which
customwas chromatographed on silica gel eluting with methanol/dichloromethane

Sources & evidence

ORD record: ord-ea0f5a79005848f2b8de938533971d6f
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812227B2

Reaction notes

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