Triethylamine → N-(3-Formyl-4-hydroxybenzoyl)phenylalanine methyl ester

HRID 1197762노트

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HRID 1197762 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[OH:27])[C:21]([OH:23])=O)=[O:17].ON1C(=O)CCC1=O.Cl.[CH3:37][O:38][C:39](=[O:49])[C@H:40]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH2:41].C(N(CC)CC)C>C(Cl)(Cl)Cl.CN(C)C=O>[CH3:37][O:38][C:39](=[O:49])[C@H:40]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:41][C:21](=[O:23])[C:20]1[CH:24]=[CH:25][C:26]([OH:27])=[C:18]([CH:16]=[O:17])[CH:19]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 80170N-HydroxysuccinimideHCID 2717613-Formyl-4-hydroxybenzoic acid

생성물 1

HCID 53719078N-(3-Formyl-4-hydroxybenzoyl)phenylalanine methyl ester

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

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온도
10 °C

실험 절차

87 mmol of dicyclohexylcarbodiimide are added to a stirred suspension, cooled to 10° C., containing 80 mmol of 3-formyl-4-hydroxybenzoic acid (prepared according to H. WYMBERG, J. Am. Chem. Soc., 76, 4998, 1954) and 87 mmol of N-hydroxysuccinimide in 320 ml of chloroform. After re-equilibrating to room temperature, the mixture is kept stirring overnight. The precipitate is then filtered. The filtrate is cooled to 8° C. and treated dropwise, with stirring, with a suspension containing 160 mmol of phenylalanine methyl ester hydrochloride and 160 mmol of triethylamine in 100 ml of anhydrous dimethylformamide. The mixture is stirred for 3 hours at 20° C. and then for 5 hours at 50° C. After cooling and evaporation of the solvents, the residue is taken up in 400 ml of ethyl acetate. After washing this solution with 1N hydrochloric acid and then with water, the organic phase is dried and evaporated. The oily residue leads to the expected product by crystallization from toluene.

후처리

  1. customAfter re-equilibrating to room temperature
  2. filtrationThe precipitate is then filtered
  3. temperatureThe filtrate is cooled to 8° C.
  4. additiontreated dropwise
  5. stirringwith stirring, with a suspension
  6. stirringThe mixture is stirred for 3 hours at 20° C.
  7. waitfor 5 hours at 50° C
  8. temperatureAfter cooling
  9. customevaporation of the solvents
  10. washAfter washing this solution with 1N hydrochloric acid
  11. dry with materialwith water, the organic phase is dried
  12. customevaporated
  13. customThe oily residue leads to the expected product by crystallization from toluene

출처 및 근거

ORD 기록
ord-78b55c1a931446239b94ae87a8b15a12
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278154

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