Triethylamine → (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

HRID 2242179Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[CH2:10][C@H:9]1[C:14]([N:16]1[CH2:20][CH2:19][S:18][CH2:17]1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(2S, 4R)-4-Hydroxy-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.34 g, 0.0111 mol, Example 17A) was dissolved in DMSO and cooled to 0° C. To the cold solution, triethylamine (7.37 g, 0.0729 mol) and sulfur trioxide pyridine complex (8.44 g, 0.0530 mol) were added. The mixture was stirred at 0° C. for 2 hours, brought to room temperature and quenched with water. The mixture was extracted with ethyl acetate and washed with 1 M HCl (60 mL), saturated NaHCO3 (2×40 mL) and brine (1×30 mL). The organic layer was dried with Na2SO4, filtered, concentrated, and purified by column chromatography (ethyl acetate/hexane, 1/1) to give the titled compound 2.05 g. MS (ESI APCI) m/e 299 (M−H)+; 1H NMR (300 MHz, methanol-d4): δ ppm 5.07 (d, 1 H), 4.80 (m, 1 H), 4.57-4.68 (m, 2 H), 4.45 (m, 1 H), 3.85 (d, 2 H), 3.78 (m, 2 H), 3.17 (t, 1 H), 3.05 (m, 2 H), 2.44-2.49 (d, 1 H), 1.47 (s, 9 H).

Workup

custombrought to room temperature
customquenched with water
extractionThe mixture was extracted with ethyl acetate
washwashed with 1 M HCl (60 mL), saturated NaHCO3 (2×40 mL) and brine (1×30 mL)
dry with materialThe organic layer was dried with Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by column chromatography (ethyl acetate/hexane, 1/1)

Sources & evidence

ORD record: ord-dcf22ebeb8e04425b800f0296bc7df2d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671076B2

Reaction notes

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