Methyl iodide → methyl (2S)-2-[(4-chlorophenyl)sulfonyl-methyl-amino]-3-hydroxy-propanoate

HRID 1479811Notes

Reaction equation

HRID 1479811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:19])[C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 131736582Methyl N-(4-chlorobenzene-1-sulfonyl)-L-serinate

Product 1

HCID 131736583methyl (2S)-2-[(4-chlorophenyl)sulfonyl-methyl-amino]-3-hydroxy-propanoateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2C (8.5 g, 28 mmol) in DMF (30 mL) was added with an. K2CO3 (1.5 mol eq, 5.99 g) and, after few minutes, iodomethane (1.2 mol eq, 3.21 mL) was added and the mixture heated at 50° C. for 12 h. The solvent was removed under reduced pressure, water was added to the residue (150 mL) and the aqueous phase extracted with EtOAc (3×60 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3C as a pale yellow oil (8.6 g, 97% yield). 1HNMR (DMSO, 200 MHz) δ 2.88 (s, 3H), 3.52 (s, 3H), 3.66 (m, 2H), 4.02 (q, 1H, J=6), 4.602 (t, 1H, J=6.1), 5.11 (t, 1H), 7.64 (d, 2H), 7.76 (d, 2H).

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue (150 mL)
  3. extractionthe aqueous phase extracted with EtOAc (3×60 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2145fbd9677248eebb7cce0b03b3d722
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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