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

HRID 581373ノート

反応式

HRID 581373 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 79724-Methylmorpholine溶媒2 回

反応条件

温度
25 °C

実験手順

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 (El): 286 (M+H+).

後処理

  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

出典と根拠

ORDレコード
ord-873717bc59254a57b7060d047ff404ed
出典データセット
uspto-grants-1999_07
特許番号
US05919949

反応ノート

読み込み中…