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

HRID 1479859Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@@H:13]([CH2:18][OH:19])[C:14]([O:16][CH3:17])=[O:15])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[K+].[K+].I[CH2:27][CH3:28]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:27][CH3:28])[C@@H:13]([CH2:18][OH:19])[C:14]([O:16][CH3:17])=[O:15])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2G (2.85 g, 8.8 mmol) in DMF (20 mL) was added with an. K2CO3 (1.5 mol eq, 1.83 g) and, after few minutes, 2-iodoethane (1.2 mol eq, 1.09 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 recombined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3G as a pale yellow oil (2.8 g, 90% yield). 1HNMR (DMSO, 200 MHz) δ 1.15 (m, 3H), 1.98 (s, 3H), 3.08 (m, 2H), 4.04 (q, 2H, J=8), 4.58 (t, 1H), 5.15 (bm, 1H), 7.71 (m, 2H), 7.94 (m, 1H).

Workup

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

Sources & evidence

ORD record: ord-c1cccc8963a24f5a8621996527740bc7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

Loading…