Hydrochloric Acid → (+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

HRID 853

反応式

HRID 853 の反応式
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C([N:14]1[CH:18]([CH2:19][OH:20])[CH2:17][O:16][C:15]1=[O:21])C.Cl.N1C=CC=[CH:25][CH:24]=1>[Cl-].[Na+].O>[CH2:24]([C:18]1([CH2:19][O:20][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH2:17][O:16][C:15](=[O:21])[NH:14]1)[CH3:25]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 19694098(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

生成物 1

HCID 18968885(+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a solution of brine and 1N HCl, stirred until solids appeared, filtered and washed with diethyl ether to give 194.6 g of a beige solid as the title product. 1H NMR consistent with the proposed structure.

後処理

  1. customto come to room temperature
  2. stirringstirred until solids
  3. filtrationfiltered
  4. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-85a305aeebfc4263a0d5dfa4da2ff2f2
出典データセット
uspto-grants-1998_03
特許番号
US05723458

関連ノート

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