4-Methylmorpholine → N-t-butoxycarbonyl-L-methionyl-L-aspartyl-D-alanine amide

HRID 596803노트

반응식

HRID 596803 반응식
CN1CCOCC1.O.[NH2:9][C@H:10]([C:15]([NH:17][C@@H:18]([C:20]([NH2:22])=[O:21])[CH3:19])=[O:16])[CH2:11][C:12](=[O:14])[OH:13].Cl.O1CCOCC1.ClC1C=C(Cl)C(Cl)=CC=1[O:39][C:40](=O)[C@H:41]([CH2:50][CH2:51][S:52][CH3:53])[NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CN(C)C=O>[C:46]([O:45][C:43]([NH:42][C@H:41]([C:40]([NH:9][C@H:10]([C:15]([NH:17][C@@H:18]([C:20]([NH2:22])=[O:21])[CH3:19])=[O:16])[CH2:11][C:12](=[O:13])[OH:14])=[O:39])[CH2:50][CH2:51][S:52][CH3:53])=[O:44])([CH3:49])([CH3:48])[CH3:47]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 13670107N-t-butoxycarbonyl-L-methionine 2,4,5-trichlorophenyl esterHCID 204431481,4-Dioxane hydrochlorideHCID 22796342L-aspartyl-D-alanine amide monohydrate

생성물 1

HCID 22796339N-t-butoxycarbonyl-L-methionyl-L-aspartyl-D-alanine amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

14.5 Parts of N-methylmorpholine is added to a stirred solution of 14.33 parts of L-aspartyl-D-alanine amide monohydrate in 189 parts of dimethylformamide and 12.6 parts by volume of a 5.60 N HCl/dioxane solution. Then, 33.2 parts of N-t-butoxycarbonyl-L-methionine 2,4,5-trichlorophenyl ester is added and the resulting mixture stirred for about 18 hours at room temperature. The solvent is removed in vacuo and the resultant syrupy oil dissolved in ethyl acetate. To this solution is added 0.82 parts of N,N-diethylaminoethylamine and the resulting mixture is stirred for about 35 minutes. The mixture is then washed twice with 5% potassium hydrogen sulfate solution, dried over anhydrous sodium sulfate, and stripped under reduced pressure to a gummy residue. The gum is triturated with ethyl ether, to yield crystals which are filtered and dried to afford N-t-butoxycarbonyl-L-methionyl-L-aspartyl-D-alanine amide. This product melts at about 107-110° C., and is represented by the following formula.

후처리

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resultant syrupy oil dissolved in ethyl acetate
  3. additionTo this solution is added 0.82 parts of N,N-diethylaminoethylamine
  4. stirringthe resulting mixture is stirred for about 35 minutes
  5. washThe mixture is then washed twice with 5% potassium hydrogen sulfate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe gum is triturated with ethyl ether
  8. customto yield crystals which
  9. filtrationare filtered
  10. customdried

출처 및 근거

ORD 기록
ord-c28d8c01df9548f6ab15d390cbac8b58
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04012367

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