Water → N-benzhydryloxycarbonyl-L-leucine

HRID 65602ノート

反応式

HRID 65602 の反応式
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[O-2].[Mg+2].O.[CH:13]([O:26][C:27](N=[N+]=[N-])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1>[CH:13]([O:26][C:27]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:28])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 6106L-LeucineHCID 76824Carbonazidic acid, diphenylmethyl esterHCID 6850729Magnesium monoxide

生成物 1

HCID 53905484N-benzhydryloxycarbonyl-L-leucine

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a mixture consisting of 13.1 g. of L-leucine, 6 g. of magnesium oxide, and 150 ml. of water is added a solution of 25.3 g. of benzhydrylazidoformate in 150 ml. of dioxane, and the resulting mixture is stirred at room temperature for 2 days. It is then filtered, and the filtrate is concentrated to remove the dioxane. The aqueous concentrate is acidified with solid citric acid, and the acidified mixture is extracted with ethyl acetate. The extract is dried and evaporated to dryness to give an oily residue of N-benzhydryloxycarbonyl-L-leucine, which is suitable for use without further purification. To a mixture of 32 g. of this intermediate product, 25 g. of pentachlorophenol, and 300 ml. of ethyl acetate, at 5° C., is added 20 g. of dicyclohexylcarbodiimide, and the resulting mixture is kept at 5° C. for 5 hours and filtered. The filtrate is concentrated to small volume, and the concentrate is treated with petroleum ether to give a precipitate of N-benzhydryloxycarbonyl-L-leucine pentachlorophenyl ester, which is isolated and crystallized from ethanol-water; m.p. 84°-86° C.; [α]D25 -27.8° (2% in methanol).

後処理

  1. filtrationIt is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto remove the dioxane
  4. concentrationThe aqueous concentrate
  5. extractionthe acidified mixture is extracted with ethyl acetate
  6. customThe extract is dried
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-425924a57b5d452b968463cd2d36b7eb
出典データセット
uspto-grants-1978_12
特許番号
US04128540

反応ノート

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