Methyl iodide → methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

HRID 1479816Notes

Reaction equation

HRID 1479816 reaction equation
[OH:1][CH2:2][C@H:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[OH:1][CH2:2][C@H:3]([N:8]([CH3:19])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6928423(S)-methyl 3-hydroxy-2-(4-methylphenylsulfonamido)propanoate

Product 1

HCID 131736587methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2E (2 g, 7.35 mmol) in DMF (15 mL) was added with an .K2CO3 (1.5 mol eq, 1.52 g) and, after few minutes, iodomethane (1.2 mol eq, 0.81 ml) was added and the mixture was heated at 50° C. overnight. The solvent was removed under reduced pressure, water was added to the residue (120 mL) and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3E as a pale yellow oil (2.1 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 2.38 (s, 3H), 2.87 (s, 3H), 3.64 (s, 3H), 3.70 (t, 2H), 4.58 (t, 1H), 5.11 (t, 1H), 7.40 (d, 2H, J=8), 7.61 (d, 2H, J=8).

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue (120 mL)
  3. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-088194fb56c64339bc0f4c99852f3336
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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