Ethylmorpholine → N-((Phenylmethoxy)carbonyl)-L-alanyl-L-alanine

HRID 47039

反応式

HRID 47039 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CC[O:22]CC1)C.C(Cl)(=O)C(C)(C)C.Br.C(N[C:36](=[O:40])[C@H:37]([CH3:39])[NH2:38])C>O1CCCC1.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:38][C@H:37]([C:36]([OH:40])=[O:22])[CH3:39])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 7525Ethylmorpholine2 回HCID 62493Pivaloyl chlorideHCID 736104N-carbobenzyloxyalanineHCID 86736706L-alanine ethylamide hydrobromide

生成物 1

HCID 7009583N-((Phenylmethoxy)carbonyl)-L-alanyl-L-alanine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-5 °C

実験手順

7.5 g (0.034 mol) of N-benzyloxycarbonyl-L-alanine were dissolved in 50 ml of dry tetrahydrofuran and the solution was cooled to -5° C. 4.26 ml (0.034 mol) of N-ethylmorpholine and 4.14 ml (0.034 mol) of pivaloyl chloride were then added and the solution was stirred at -5° C. for 30 minutes. To this mixture was then added a solution of 7.0 g (0.034 mol) of L-alanine ethylamide hydrobromide in 50 ml of dimethylformamide followed by 8.5 ml (0.068 mol) of N-ethylmorpholine. The solution was stirred at -10° C. for 1 hour and then left to stand for 16 hours at room temperature. The solvents were removed by evaporation; the product crystallising on the addition of water. The yield of N-benzyloxycarbonyl-L-alanyl-L-alanine obtained was 9.05 g (83%); melting point 203°-205° C.; [α]D20 =-1.1° (c=1.02% in dimethylformamide; [α] 36520 =-9.2° (c=1.02% in dimethylformamide).

後処理

  1. stirringThe solution was stirred at -10° C. for 1 hour
  2. waitleft
  3. waitto stand for 16 hours at room temperature
  4. customThe solvents were removed by evaporation
  5. customthe product crystallising on the addition of water

出典と根拠

ORDレコード
ord-ffe30715d2234adfab12f8449f2baa6b
出典データセット
uspto-grants-1979_11
特許番号
US04176116

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