Methyl iodide → methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

HRID 1479816ノート

反応式

HRID 1479816 の反応式
[OH:1][CH2:2][C@H:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[OH:1][CH2:2][C@H:3]([N:8]([CH3:19])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6928423(S)-methyl 3-hydroxy-2-(4-methylphenylsulfonamido)propanoate

生成物 1

HCID 131736587methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A solution of 2E (2 g, 7.35 mmol) in DMF (15 mL) was added with an .K2CO3 (1.5 mol eq, 1.52 g) and, after few minutes, iodomethane (1.2 mol eq, 0.81 ml) was added and the mixture was heated at 50° C. overnight. The solvent was removed under reduced pressure, water was added to the residue (120 mL) and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3E as a pale yellow oil (2.1 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 2.38 (s, 3H), 2.87 (s, 3H), 3.64 (s, 3H), 3.70 (t, 2H), 4.58 (t, 1H), 5.11 (t, 1H), 7.40 (d, 2H, J=8), 7.61 (d, 2H, J=8).

後処理

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue (120 mL)
  3. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-088194fb56c64339bc0f4c99852f3336
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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