L-Serine, methyl ester, hydrochloride (1:1) → methyl (2S)-2-[(3-fluorophenyl)sulfonylamino]-3-hydroxy-propanoate
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[F:10][C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1>C(Cl)Cl>[F:10][C:11]1[CH:12]=[C:13]([S:17]([NH:6][C@@H:5]([CH2:7][OH:8])[C:4]([O:3][CH3:2])=[O:9])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1Participants
Procedure
A suspension of L-serine-methyl ester hydrochloride (1.6 g, 10.3 mmol) in CH2Cl2 (70 mL) was added with TEA (1.1 mol eq, 1.6 mL) and the mixture was stirred at r.t. for 10 minutes. Then 3-fluorobenzensulfonyl chloride (1 mol eq, 2.0 g) and additional TEA (1.1 mol eq) were added and the solution hated at 60° C. overnight. The solvent was removed under reduced pressure, water was added to the residue (100 mL) and the aqueous phase extracted with EtOAc (3×40 mL). The recombined organic phases were dried over Na2SO4 and evaporated to reduced pressure. The residue was recrystallized from ethylic ether to afford 2F as a pale yellow solid (2.80 g, 95% yield). 1HNMR (DMSO, 200 MHz) δ 3.41 (s, 3H), 3.48 (m, 2H), 4.01 (m, 1H), 5.20 (t, 1H), 7.58 (m, 2H), 7.81 (m, 2H), 8.52 (d, 1H, J=8).
Workup
- additionwas added with TEA (1.1 mol eq
- waitthe solution hated at 60° C. overnight
- customThe solvent was removed under reduced pressure, water
- additionwas added to the residue (100 mL)
- extractionthe aqueous phase extracted with EtOAc (3×40 mL)
- dry with materialThe recombined organic phases were dried over Na2SO4
- customevaporated to reduced pressure
- customThe residue was recrystallized from ethylic ether
Sources & evidence
- ORD record
- ord-41a2d8821387441980bc003953b8d285
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409864B2
Reaction notes
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