L-Aspartic Acid → N-(1-methylcyclobutyloxycarbonyl) aspartic acid dimethyl ester

HRID 1605179ノート

反応式

HRID 1605179 の反応式
COC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](CC(=O)O)N.[CH3:22][C:23]1([O:27][C:28](N[C@@H]2C(=O)OC(=O)C2)=[O:29])[CH2:26][CH2:25][CH2:24]1.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N.N[C@H](C(O)=O)CC(O)=O.[CH3:61][O:62][C:63](=[O:71])[C@H:64]([CH2:66][C:67]([O:69][CH3:70])=[O:68])[NH2:65].ClC([O-])=O.ClC(OC1(C)CCC1)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:61][O:62][C:63](=[O:71])[C@H:64]([CH2:66][C:67]([O:69][CH3:70])=[O:68])[NH:65][C:28]([O:27][C:23]1([CH3:22])[CH2:26][CH2:25][CH2:24]1)=[O:29]

参加物

10

反応物 7

HCID 5960L-Aspartic Acid2 回HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 1112071,4-Dimethyl L-aspartate2 回HCID 134601AspartameHCID 21226386CarbonochloridateHCID 215491141-Methylcyclobutyl ChloroformateHCID 54330780N-(1-Methylcyclobutyloxycarbonyl)-Aspartic Anhydride

生成物 1

HCID 54510473N-(1-methylcyclobutyloxycarbonyl) aspartic acid dimethyl ester

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 8471Triethylamine溶媒

実験手順

An example of the use of the novel N-protected-α-amino acid compounds of this invention in peptide synthesis is the preparation of α-aspartyl-phenylalanine methyl ester, a known sweetening agent. The dipeptide is conveniently prepared by coupling N-(1-methylcyclobutyloxycarbonyl) aspartic anhydride with phenylalanine methyl ester hydrochloride. Introduction of the N-(1-methylcyclobutyloxycarbonyl blocking group into aspartic acid is accomplished by reacting 1-methylcyclobutylchloroformate with aspartic acid dimethyl ester in accordance with the process of this invention. Equimolar quantities of the chloroformate and aspartic acid dimethyl ester are reacted in chloroform at 0°C. at pH 8. Reaction is carried out by portion-wise addition of 1-methylcyclobutyl chloroformate to the aspartic acid suspended in chloroform. Triethylamine is added to the reaction during the addition to maintain pH 8. After allowing the reaction to run to completion at room temperature, the reaction mixture is treated according to the procedure outlined above to afford the N-(1-methylcyclobutyloxycarbonyl) aspartic acid dimethyl ester. The free acid is obtained by saponifying the ester in a basic aqueous methanol solution. After acidifying the reaction mixture with sulfuric acid, the N-(1-methylcyclobutyloxycarbonyl) aspartic acid is isolated by extraction.

後処理

  1. customReaction
  2. temperatureto maintain pH 8
  3. customthe reaction
  4. customto run to completion at room temperature
  5. additionthe reaction mixture is treated

出典と根拠

ORDレコード
ord-b51c28ba7a6747918b78e74685af91d4
出典データセット
uspto-grants-1976_04
特許番号
US03948971

反応ノート

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