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

HRID 20364

반응식

HRID 20364 반응식
[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]

참가 물질

5

반응물 3

HCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 86587134Acetonitrile dry iceHCID 178419574HCID 178419574, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-35 °C

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-0fe8c878f3af4269b56cb8110fc22ece
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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