Ethyl Acetate → methanesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester

HRID 2209749노트

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HRID 2209749 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C@H:13]1[C@@H:17]([CH2:18][OH:19])[O:16][C:15](=[O:20])[NH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+].C(OCC)(=O)C>CC(C)=O.CN1CCOCC1>[CH2:6]([C@H:13]1[C@@H:17]([CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[O:16][C:15](=[O:20])[NH:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

생성물 1

HCID 57150902methanesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester수율 100%

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 79724-Methylmorpholine용매2회

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온도
25 °C

실험 절차

A solution of 4.7 ml of methanesulphonyl chloride in 10 ml of acetone is added at 25° C. to a suspension of 10.4 g of the alcohol from Example 8 in 20 ml of acetone and 6.1 ml of N-methylmorpholine and the suspension is stirred at 25° C. for 3 hours. A further 1.1 ml of N-methylmorpholine are added and the mixture is stirred for 1 hour. The suspension is shaken with 80 ml of semi-saturated NaHCO3 solution and ethyl acetate and the separated aqueous phase is extracted with ethyl acetate. The ethyl acetate extracts are washed with water, dried and filtered. The filtrate is concentrated to give 14.3 g (100%) of crude methanesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, TLC (SiO2 ethyl acetate): Rf =0.4; MS (EI): 286 (M+H+).

후처리

  1. stirringthe mixture is stirred for 1 hour
  2. extractionthe separated aqueous phase is extracted with ethyl acetate
  3. washThe ethyl acetate extracts are washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated

출처 및 근거

ORD 기록
ord-926bb4d63826446a99a579960a14c07c
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455353

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