Hydrochloric Acid → S-(4-Methylbenzyl)-L-Cysteine t-Butyl Ester

HRID 1651713ノート

反応式

HRID 1651713 の反応式
[CH3:1][C:2](=[CH2:4])[CH3:3].[CH3:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][S:11][CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[CH:8][CH:7]=1.OS(O)(=O)=O.[OH-].[Na+].Cl>O1CCOCC1.CCOCC>[C:2]([O:17][C:15](=[O:16])[C@H:13]([CH2:12][S:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([CH3:5])=[CH:19][CH:18]=1)[NH2:14])([CH3:3])([CH3:1])[CH3:4]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 13994756S-p-Methylbenzyl-L-cysteine

生成物 1

HCID 14770807S-(4-Methylbenzyl)-L-Cysteine t-Butyl Ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a cold solution of isobutylene (50 ml) in dioxane (80 ml), add S-(4-methylbenzyl)-L-cysteine (5.0 g) and concentrated H2SO4 (10 ml). Seal the vessel, allow to warm to room temperature, and stir for 18 hr. Pour into 5% NaOH (500 ml), extract with Et2O (3×400 ml), dry (MgSO4) and concentrate the Et2O in vacuo to give an oil. Treat the oil with HCl in Et2O to give the title compound, white needles (2.76 g) m.p. 218° (dec).

後処理

  1. customSeal the vessel
  2. extractionextract with Et2O (3×400 ml)
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate the Et2O in vacuo
  5. customto give an oil

出典と根拠

ORDレコード
ord-7b04dbd7580448f2be6f0002e56d6b62
出典データセット
uspto-grants-1990_05
特許番号
US04929641

反応ノート

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