4-Toluenesulfonyl chloride → (R)-2-Tosyloxypropionic acid methyl ester

HRID 1802855노트

반응식

HRID 1802855 반응식
[C:1]([O:6][CH3:7])(=[O:5])[C@@H:2]([CH3:4])[OH:3].C(N(CC)CC)C.Cl.CN(C)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(#N)C>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:3][C@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])(=[O:28])=[O:27])=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 637514(+)-Methyl lactateHCID 10313079Trimethylamine Hydrochloride

생성물 1

HCID 12884153(R)-2-Tosyloxypropionic acid methyl ester수율 87.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A solution of methyl (R)-(+)-lactate (6.66 g) in acetonitrile (33 ml) was cooled to 5° C. and triethylamine (9.8 ml) added followed by trimethylamine hydrochloride (0.62 g). A separate solution of p-toluenesulfonyl chloride (11.6 g) in acetonitrile (33 ml) was added dropwise over 20 min maintaining the temperature below 5° C. The reaction mixture was filtered and concentrated. Diethylether and water were added and the organic fraction dried (MgSO4) and concentrated in vacuo to give the sub-title compound as a yellow oil (13.71 g).

후처리

  1. temperaturemaintaining the temperature below 5° C
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. additionDiethylether and water were added
  5. dry with materialthe organic fraction dried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1dee591e59984c49be2d460f71e9265a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349897B2

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