Trimethylamine → HCID 13477575, 화합물

HRID 370624

반응식

HRID 370624 반응식
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.Cl.[CH3:15][O:16][C:17](=[O:24])[CH2:18][CH2:19][C@H:20]([NH2:23])[CH2:21][F:22].CN(C)C.C1(N=C=NC2CCCCC2)CCCCC1>C(O)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:23][C@H:20]([CH2:21][F:22])[CH2:19][CH2:18][C:17]([O:16][CH3:15])=[O:24])=[O:8]

참가 물질

7

반응물 4

HCID 1146TrimethylamineHCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 131714255(S)-4-amino-5-fluoropentanoic acid methyl ester, hydrochloride

생성물 1

HCID 13477575HCID 13477575, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 6344Dichloromethane용매

실험 절차

0.70 g of 2,4-dichlorophenoxyacetic acid, 0.59 g of 4 and 0.44 ml of trimethylamine were mixed with 75 ml of methylene chloride, and the mixture was stirred at room temperature for 30 minutes. Then, 0.65 g of N,N'-dicyclohexylcarbodiimide was added and the mixture was stirred at room temperature overnight. Several drops of glacial acetic acid were added and the mixture was filtered. The filtrate was washed successively with water, 1N hydrochloric acid, and half-saturated aqueous sodium bicarbonate solution, dried (Na2SO4) and stripped of solvent. The residue was triturated with ethyl acetate, the mixture was filtered and the solvent was evaporated from the filtrate under reduced pressure. The solid residue was triturated with hexane, the mixture was filtered and the solvent was evaporated from the filtrate. The solid residue was chromatographed over silica gel, first with a 1:3 v:v mixture of ethyl acetate and hexane as eluent, then with a 1:1 v:v mixture of ethyl acetate and hexane as eluent. On workup, 16 was obtained, as a white solid.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationthe mixture was filtered
  3. washThe filtrate was washed successively with water, 1N hydrochloric acid, and half-saturated aqueous sodium bicarbonate solution
  4. dry with materialdried (Na2SO4)
  5. customThe residue was triturated with ethyl acetate
  6. filtrationthe mixture was filtered
  7. customthe solvent was evaporated from the filtrate under reduced pressure
  8. customThe solid residue was triturated with hexane
  9. filtrationthe mixture was filtered
  10. customthe solvent was evaporated from the filtrate
  11. customThe solid residue was chromatographed over silica gel, first with a 1:3 v
  12. additionv mixture of ethyl acetate and hexane as eluent
  13. additionwith a 1:1 v:v mixture of ethyl acetate and hexane as eluent
  14. customOn workup, 16 was obtained, as a white solid

출처 및 근거

ORD 기록
ord-5a6c45bef63a4c6ba8582ea58a66896b
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04528028

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