Lactic Acid → HCID 86740463、化合物

HRID 621122ノート

反応式

HRID 621122 の反応式
[CH3:1][O:2][C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10][OH:11])[C@H:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]1=[O:22].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(O)(=O)C(C)O>N1C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10][O:11][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[C@H:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]1=[O:22]

参加物

7

反応物 3

HCID 612Lactic AcidHCID 73974-Toluenesulfonyl chlorideHCID 70390815HCID 70390815、化合物

生成物 1

HCID 86740463HCID 86740463、化合物収率 91.2%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Under stirring at 0° C., 1.73 g of cis-1-(2,4-dimethoxybenzyl)-4-hydroxymethyl-3-phenylacetamido-2-oxoazetidine is added to a solution of 1.12 g of p-toluenesulfonyl chloride in 6 ml of pyridine. The reaction mixture is stirred for 2 hours and then allowed to stand overnight in a refrigerator. To the reaction mixture is added 0.68 ml of lactic acid and the mixture is stirred for one hour. The reaction mixture is diluted with 45 ml of ethyl acetate and 15 ml of tetrahydrofuran, and then washed with dilute hydrochloric acid, and aqueous sodium chloride solution, an aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution in this order. The organic solution is dried over magnesium sulfate and the solvent is distilled off in vacuo. To the residue is added a mixed solvent of ether and ethyl acetate (5:1) and the resulting crystals are collected by filtration to give 2.21 g (91%) of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-4-(p-toluenesulfonyloxymethyl)-2-oxoazetidine, m.p. 109°-110° C.

後処理

  1. stirringThe reaction mixture is stirred for 2 hours
  2. stirringthe mixture is stirred for one hour
  3. washwashed with dilute hydrochloric acid, and aqueous sodium chloride solution
  4. dry with materialThe organic solution is dried over magnesium sulfate
  5. distillationthe solvent is distilled off in vacuo
  6. additionTo the residue is added a mixed solvent of ether and ethyl acetate (5:1)
  7. filtrationthe resulting crystals are collected by filtration

出典と根拠

ORDレコード
ord-6d46177976c94abd8c180f8b1e94c836
出典データセット
uspto-grants-1989_04
特許番号
US04822788

反応ノート

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