Iodoethane → methyl (2S)-2-[(3-fluorophenyl)sulfonyl-ethyl-amino]-3-hydroxy-propanoate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:26][CH3:27]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]([CH2:26][CH3:27])[C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2F (3.0 g, 10.8 mmol) in DMF (15 mL) was added with an. K2CO3 (1.5 mol eq, 2.24 g) and, after few minutes, 2-iodoethane (1.2 mol eq, 1.33 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 (4×50 mL). The recombined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3F as a pale orange viscous oil (3.2 g, 95% yield). 1HNMR (DMSO, 200 MHz) δ 1.15 (m, 3H), 2.00 (s, 3H), 3.79 (q, 2H, J=8), 4.06 (t, 1H), 4.59 (t, 1H), 5.18 (m, 2H), 7.94 (m, 4H).
Workup
- customThe solvent was removed under reduced pressure, water
- additionwas added to the residue (150 mL)
- extractionthe aqueous phase extracted with EtOAc (4×50 mL)
- dry with materialThe recombined organic phases were dried over Na2SO4
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-5e33db35668c4758a3b636f612eb96b7
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409864B2
Reaction notes
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