Phosphorus trichloride → N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

HRID 325270노트

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HRID 325270 반응식
[C:1]([NH:7][C@H:8]([C:13]([O-:15])=O)[CH2:9][C:10]([O-:12])=[O:11])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Na+].[Na+].P(Cl)(Cl)Cl.C(N[C@@H]1C(=O)OC(=O)C1)(=O)CC(C)=O.[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH2:40]>O1CCOCC1.C(O)(=O)C.C(OCC)(=O)C>[CH3:36][O:37][C:38](=[O:48])[C@H:39]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:40][C:13](=[O:15])[C@H:8]([CH2:9][C:10](=[O:11])[OH:12])[NH:7][C:1](=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

참가 물질

8

반응물 4

HCID 24387Phosphorus trichlorideHCID 736234L-Phenylalanine, methyl esterHCID 13334674N-acetoacetyl-L-aspartic anhydrideHCID 86739332Disodium N-acetoacetylaspartate

생성물 1

HCID 13334676N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

Crude disodium N-acetoacetylaspartate, 28.51 parts, was stirred with 200 parts by volume of ethyl acetate and 11.7 parts by volume of acetic acid at 0°-5° C. under argon while 4.37 parts by volume of phosphorous trichloride was added dropwise. The resulting mixture was allowed to warm to ambient temperatures while stirring for 20 hours. To the resulting solution which contains N-acetoacetyl-L-aspartic anhydride was added dropwise over a 2 hour period 122 parts by volume of 0.9 M L-phenylalanine methyl ester in dioxane. After continued stirring for 20 hours, the solvent was evaporated under vacuum at 35°-40° C. Toluene, 200 parts by volume, was added to the residue and the evaporation was repeated, giving crude N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester as a semi-solid yellow residue.

후처리

  1. additionwas added dropwise
  2. temperatureto warm to ambient temperatures
  3. stirringAfter continued stirring for 20 hours
  4. customthe solvent was evaporated under vacuum at 35°-40° C
  5. additionToluene, 200 parts by volume, was added to the residue
  6. customthe evaporation

출처 및 근거

ORD 기록
ord-ae02da52df18469f80af1069646dabb4
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440677

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