Ethylmorpholine → L-glutamylphenylalanine benzyl ester

HRID 255581ノート

反応式

HRID 255581 の反応式
[NH2:1][C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH2:22]([O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.ClCCl>[CH2:22]([O:29][C:30](=[O:40])[C@H:31]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:32][C:8](=[O:10])[C@H:2]([CH2:3][CH2:4][C:5](=[O:6])[OH:7])[NH2:1])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

7

反応物 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 33032L-Glutamic AcidHCID 86587548L-phenylalanine benzyl ester toluenesulfonic acid

生成物 1

HCID 86741776L-glutamylphenylalanine benzyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 0.52 g of pyro-L-glutamic acid, 1.72 g of L-phenylalanine benzyl ester toluenesulfonic acid and 0.55 mg of N-ethylmorpholine in 5 ml of dimethylformamide (DMF) and 20 ml of dichloromethane was cooled in an ice bath with stirring. A solution of 0.826 g of dicyclohexylcarbodiimide in 2 ml dichloromethane was added to the above reaction mixture. The reaction mixture was stirred in an ice water bath for 1 hour and then at room temperature overnight. Dicyclohexylurea was removed by filtration and the product was washed in ethyl acetate. Solvents of the combined filtrates were removed under reduced pressure with a rotary evaporator at 40° C. Ethyl acetate (25 ml) was added to the residue and the organic solution was washed until neutral. The organic phase was dried over anhydrous MgSO4, filtered and then the solvent was removed with a rotary evaporator. The material was crystalized from isopropanol and ether, yield: 1.01 g of white needles, m.p. 103°-104.5° C. The material was homogeneous on all TLC and electrophoresis systems.

後処理

  1. stirringThe reaction mixture was stirred in an ice water bath for 1 hour
  2. customat room temperature
  3. customovernight
  4. customDicyclohexylurea was removed by filtration
  5. washthe product was washed in ethyl acetate
  6. customSolvents of the combined filtrates were removed under reduced pressure with a rotary evaporator at 40° C
  7. additionEthyl acetate (25 ml) was added to the residue
  8. washthe organic solution was washed until neutral
  9. dry with materialThe organic phase was dried over anhydrous MgSO4
  10. filtrationfiltered
  11. customthe solvent was removed with a rotary evaporator
  12. customThe material was crystalized from isopropanol and ether, yield: 1.01 g of white needles, m.p. 103°-104.5° C

出典と根拠

ORDレコード
ord-85e67061134749ae84cc430c75813317
出典データセット
uspto-grants-1987_10
特許番号
US04698355

反応ノート

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