Iodoethane → ethyl (2S)-2-[(4-chlorophenyl)sulfonyl-ethyl-amino]-3-hydroxy-propanoate

HRID 1479814Notes

Reaction equation

HRID 1479814 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+].[CH2:25](I)[CH3:26]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:25][CH3:26])[C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH2:16][CH3:19])=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 131736582Methyl N-(4-chlorobenzene-1-sulfonyl)-L-serinate

Product 1

HCID 131736585ethyl (2S)-2-[(4-chlorophenyl)sulfonyl-ethyl-amino]-3-hydroxy-propanoateYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 2C (1.65 g, 5.6 mmol) dissolved in DMF (15 ml) was added with K2CO3 (1.1 equiv., 854 mg) and ethyl iodide (1.1 equiv., 0.63 ml) and the reaction was stirred at rt overnight. The reaction was diluted with ethyl acetate and washed several times with water and finally with Brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from ethyl ether and petroleum ether afforded 1.6 g of a semisolid. Yield=88%. 1HNMR (DMSO, 200 MHz) δ 1.00 (3H, d, J=6.2 Hz), 3.32 (3H, s), 3.34 (2H, m), 3.75 (2H, m), 4.42 (1H, t), 5.08 (1H, bs), 7.62 (2H, m), 7.76 (2H, m)

Workup

  1. washwashed several times with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe purification of the crude residue
  5. customby crystallization from ethyl ether and petroleum ether

Sources & evidence

ORD record
ord-77004c7da67a4ed7bcd000a6a17f6c00
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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