HCID 86641981, compound → L-Leucine, N-(methylsulfonyl)-

HRID 2363554Notes

Reaction equation

HRID 2363554 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][C@H:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:5]([O:7]C(C)(C)C)=[O:6]>Cl.O1CCOCC1>[CH3:1][CH:2]([CH3:17])[CH2:3][C@H:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 86641981HCID 86641981, compound

Product 1

HCID 2448000L-Leucine, N-(methylsulfonyl)-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl 2-amino-4-methylpentanoate hydrochloride (1.53 g, 6.84 mmol) was dissolved in dichloromethane and triethylamine (3.15 mL, 22.57 mmol). Methanesulfonyl chloride (0.638 mL, 8.21 mmol) was added dropwise, and the reaction stirred at room temperature for 1 hour. The reaction was quenched with saturated aqueous NaHCO3 and extracted with dichloromethane (3×50 mL). The solvent was removed in vacuo to give (S)-tert-butyl 4-methyl-2-(methylsulfonamido)pentanoate: 1H NMR (300 MHz, CDCl3) δ ppm 4.71 (d, J=9.7, 1H), 3.98 (td, J=9.5, 5.5, 1H), 2.92 (s, 3H), 1.84 (dt, J=13.1, 6.6, 1H), 1.54 (s, 9H), 1.44-1.48 br s, 1H), 0.96 (dd, J=6.6, 2.4, 6H); MS (ESI−) m/z 264 (M−H)−. (S)-tert-Butyl 4-methyl-2-(methylsulfonamido)pentanoate was dissolved in 10 mL of 4 N HCl in dioxane and stirred at room temperature overnight. The solvent was removed under a stream of nitrogen and under high vacuum to give (S)-4-methyl-2-(methylsulfonamido)pentanoic acid: 1H NMR (300 MHz, CDCl3) δ ppm 4.86 (d, J=9.6, 1H), 4.17 (td, J=9.6, 4.8, 1H), 3.18-3.07 (m, 1H), 2.99 (s, 3H), 1.96-1.80 (m, 1H), 1.64 (dddd, J=23.4, 13.9, 9.1, 5.0, 2H), 1.40 (t, J=7.3, 1H), 0.98 (dd, J=6.6, 3.3, 6H).

Workup

  1. customThe solvent was removed under a stream of nitrogen and under high vacuum

Sources & evidence

ORD record
ord-7df20d651d0749e7858301d0d1882b7a
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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