Pyridine → N-[1-(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxyanhydride

HRID 1009812

반응식

HRID 1009812 반응식
O.O.P([O-])(O)(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[CH2:15]([O:17][C:18]([C@@H:20]([NH:29][C@H:30]([C:32]([OH:34])=[O:33])[CH3:31])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[CH3:16].Cl[C:36](Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>O.ClCCl>[CH3:16][CH2:15][O:17][C:18]([CH:20]([N:29]1[C:36](=[O:38])[O:34][C:32](=[O:33])[CH:30]1[CH3:31])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 94429TriphosgeneHCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanineHCID 131728993Disodium dihydrogen phosphate dihydrate

생성물 1

HCID 4639425N-[1-(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxyanhydride

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

Disodium dihydrogen phosphate dihydrate (177 gms; 0.994 moles) was dissolved in water (300 ml) at 35° C. and cooled to ambient temperature. Dichloromethane (250 ml) was charged and stirred for 15 mins. N-[1-(S)-ethoxy carbonyl-3-phenyl propyl]-L-alanine (106 gms; 0.381 moles) was added to the above solution and the reaction mass was cooled to 15° C. Solution of triphosgene (52.8 gms; 0.177 moles) dissolved dichloromethane (40 ml) was added dropwise to the reaction mass in 40 mins at 15-20° C. The reaction mass was further stirred for 30 min. Pyridine (0.5 ml; 0.006 moles) was added and the reaction mass was stirred for 1 hr at 15-20° C. The reaction mass was settled and layers were separated. Organic layer was washed with 2N HCl till the neutral pH obtained. The organic layer was further washed with water and dried over sodium sulphate. The solvent was evaporated to residue (110 gms).

후처리

  1. temperaturethe reaction mass was cooled to 15° C
  2. additionwas added dropwise to the reaction mass in 40 mins at 15-20° C
  3. stirringThe reaction mass was further stirred for 30 min
  4. stirringthe reaction mass was stirred for 1 hr at 15-20° C
  5. customlayers were separated
  6. washOrganic layer was washed with 2N HCl till the neutral pH
  7. customobtained
  8. washThe organic layer was further washed with water
  9. dry with materialdried over sodium sulphate
  10. customThe solvent was evaporated to residue (110 gms)

출처 및 근거

ORD 기록
ord-f600f994792b486984d622730424ab60
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973173B2

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