Heptane → methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate

HRID 2209714Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH3:24]CCCCCC>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@H:13]([CH:14]([CH3:16])[CH3:15])[C:17]([O:19][CH3:24])=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of N-[4-methoxybenzenesulfonyl]-(D)-valine (8369 g, 29.13 mol) in methanol (30 L) at 5° C. is added thionyl chloride (2176 mL, 29.7 mol) over 2.5 hours. After stirring for 3 hours at 5° C., the reaction is stirred for 36 hours at room temperature. Most of the solvent is evaporated, and the chide product is dissolved in toluene (80 L). The toluene layer is then washed with water (20 L), saturated sodium bicarbonate (20 L), water again (20 L), 2N hydrochloric acid (20 L), brine (20 L), dried (Na2SO4), and the solvent is evaporated. The solid obtained is dissolved in ethyl acetate (8 L) and heptane (16 L) is added to induce crystallization. The precipitated product is collected by filtration to provide methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate.

Workup

stirringthe reaction is stirred for 36 hours at room temperature
customMost of the solvent is evaporated
dissolutionthe chide product is dissolved in toluene (80 L)
washThe toluene layer is then washed with water (20 L), saturated sodium bicarbonate (20 L), water again (20 L), 2N hydrochloric acid (20 L), brine (20 L)
dry with materialdried (Na2SO4)
customthe solvent is evaporated
customThe solid obtained
customcrystallization
filtrationThe precipitated product is collected by filtration

Sources & evidence

ORD record: ord-1af787fbae9e4395888bd102c6fccb6f
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455258

Reaction notes

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