Oxiranemethanol, 4-methylbenzenesulfonate, (S)- → Toluene-4-sulfonic acid (s)-2-hydroxy-4-phenylbutyl ester

HRID 20364

反応式

HRID 20364 の反応式
[C:1]1([Mg]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[C:10](#N)C.C(=O)=O.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:26][CH2:27][C@H:28]2[O:30][CH2:29]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>O1CCCC1>[OH:30][C@@H:28]([CH2:29][CH2:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:27][O:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

参加物

5

反応物 3

HCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 86587134Acetonitrile dry iceHCID 178419574HCID 178419574、化合物

生成物 1

HCID 11209409Toluene-4-sulfonic acid (s)-2-hydroxy-4-phenylbutyl ester収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-35 °C

実験手順

Add phenyl methyl magnesium bromide (14 mL, 14 mmol, 1 M in tetrahydrofuran) to a solution of lithium tetrachlorocuprate (5.5 mL, 0.55 mmol, 0.1 M in tetrahydrofuran) in dry tetrahydrofuran (10 mL) and stir at −35° C. (acetonitrile/dry ice bath) for 15 minutes (J. Med. Chem., 41, 2451-2460, (1998); JOC, 54, 1295-1304, (1989)). Cool to −35° C. a solution of (2S)-(+)-glycidyl tosylate (2.51 g, 11.0 mmol) in dry tetrahydrofuran (4 mL) and transfer rapidly via cannula to the Grignard solution. Stir for 1 hour at −35° C., quench with a saturated aqueous ammonium chloride solution and dilute with diethyl ether. Wash the organic layer with saturated aqueous sodium chloride, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes) to give the desired compound as a colorless oil (1.77 g, 50%)

後処理

  1. customquench with a saturated aqueous ammonium chloride solution
  2. additiondilute with diethyl ether
  3. washWash the organic layer with saturated aqueous sodium chloride
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-0fe8c878f3af4269b56cb8110fc22ece
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

読み込み中…