N,N-Dimethylglycine → 3-O-(N,N-dimethylaminoacetyl)-1,2-O-dioleylglycerol

HRID 376424

반응식

HRID 376424 반응식
CN(C)C=O.[CH3:6][N:7]([CH3:12])[CH2:8][C:9]([OH:11])=[O:10].C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.[CH2:34]([O:52][CH2:53][CH:54]([CH2:74]O)[O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]/[CH:64]=[CH:65]\[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>C(Cl)Cl>[CH3:6][N:7]([CH2:8][C:9]([O:11][CH2:74][CH:54]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]/[CH:64]=[CH:65]\[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH2:53][O:52][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:10])[CH3:12]

참가 물질

7

반응물 5

HCID 673N,N-DimethylglycineHCID 1049PyridineHCID 6228DimethylformamideHCID 10868Dicyclohexylcarbodiimide2회HCID 53803432,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanol

생성물 1

HCID 867518613-O-(N,N-dimethylaminoacetyl)-1,2-O-dioleylglycerol수율 67.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a solvent mixture of 22 ml N,N-dimethylformamide and 11 ml methylene chloride was suspended 572 mg (5.547 mmol) of N,N-dimethylglycine followed by addition of 1736 mg (8.414 mmol) of N,N'-dicyclohexylcarbodiimide and the mixture was stirred at ambient temperature overnight. The solvent was then distilled off under reduced pressure and the residue was dissolved in 12 ml of pyridine containing 327 mg (0.551 mmol) of dissolved 1,2-O-dioleylglycerol. Then, 80 mg (0.388 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was added and the reaction was conducted at 50° C. overnight. After completion of the reaction, the solvent was distilled off and the residue was dissolved in methylene chloride, washed with saturated aqueous sodium hydrogen carbonate solution, dried, and concentrated. The residue was subjected to column chromatography (silica gel/ethyl acetate-n-hexane) to provide 251 mg (67.2%) of the title compound of the invention.

후처리

  1. distillationThe solvent was then distilled off under reduced pressure
  2. waitthe reaction was conducted at 50° C. overnight
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ac7842d3bebd45c1bccd168494de1b15
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020317

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