Hydrochloric Acid → HCID 66674378, compound

HRID 426421Notes

Reaction equation

[CH:1]1([CH2:7][CH:8]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][C@@H](O)S([O-])(=O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].CO.Cl.CO[CH:26]([O:29][CH3:30])[O:27][CH3:28]>O1CCOCC1>[CH3:19][O:18][C:16](=[O:17])[C@@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH2:9][CH:26]([O:27][CH3:28])[O:29][CH3:30]

Participants

Conditions

Temperature: 50 °C

Procedure

To a slurry of sodium (S)-4-cyclohexyl-1-hydroxy-3-methoxycarbonyl-butane-1-sulfonate (400.0 g, 1.26 mol) and methanol (2 L) was added 4.0 M HCl in 1,4-dioxane (400 mL) and the reaction mixture was stirred for 15 min. Trimethoxymethane (340 mL, 3.11 mol) was added and reaction mixture was heated at 50° C. overnight, and then cooled to room temperature. White solids were filtered off and discarded. Most of the solvent was removed from the filtrate by rotary evaporation. Ethyl acetate (800 mL) was added resulting in more precipitation. The white precipitate was removed by filtration. Solvent was removed from the filtrate by rotary evaporation and then under high vacuum at room temperature overnight to yield the title compound (211 g) as a thick oil. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 4.25 (t, 1H), 3.57 (s, 3H), 3.18 (s, 6H), 2.43 (m, 1H), 1.55-1.81 (m, 2H), 1.50-1.72 (m, 5H), 1.20-1.48 (m, 2H), 1.05-1.21 (m, 4H), 0.71-0.92 (m, 2H).

Workup

customreaction mixture
temperaturecooled to room temperature
filtrationWhite solids were filtered off
customMost of the solvent was removed from the filtrate by rotary evaporation
additionEthyl acetate (800 mL) was added
customresulting in more precipitation
customThe white precipitate was removed by filtration
customSolvent was removed from the filtrate by rotary evaporation

Sources & evidence

ORD record: ord-00f377b5d78a4ba78a8e2283472e0444
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106232B2

Reaction notes

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