(2S)-(-)-1-Amino-3-phenoxy-2-propanol → dimethyl 4-[2-[(E)-4-[[(S)-2-hydroxy-3-phenoxypropyl]amino]-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate HCl salt

HRID 4670노트

반응식

HRID 4670 반응식
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:18]([CH3:27])=[C:17]1[C:28]([O:30][CH3:31])=[O:29].[OH:32][C@H:33]([CH2:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][NH2:35]>C(#N)C>[ClH:1].[OH:32][C@H:33]([CH2:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][NH:35][CH2:2]/[CH:3]=[CH:4]/[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([CH3:26])[NH:19][C:18]([CH3:27])=[C:17]1[C:28]([O:30][CH3:31])=[O:29]

참가 물질

4

반응물 2

HCID 1133101(2S)-(-)-1-Amino-3-phenoxy-2-propanolHCID 14050497dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

생성물 1

HCID 14050474dimethyl 4-[2-[(E)-4-[[(S)-2-hydroxy-3-phenoxypropyl]amino]-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate HCl salt수율 42.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3.1 g of dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 5.8 g (S)-2-hydroxy-3-phenoxypropylamine were dissolved in 35 ml of acetonitrile, and the resultant solution was refluxed under heating for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in 30 ml of chloroform. After washing the solution with water three times, the organic layer was concentrated under reduced pressure. The residue obtained was subjected to column chromatography on silica gel. The product was eluted with chloroform-methanol (95:5 V/V), was converted to HCl salt, and then was treated with ether-ethyl acetate to give 1.8 g of dimethyl 4-[2-[(E)-4-[[(S)-2-hydroxy-3-phenoxypropyl]amino]-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate HCl salt.

후처리

  1. temperatureunder heating for 2 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 30 ml of chloroform
  4. washAfter washing the solution with water three times
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue obtained
  7. washThe product was eluted with chloroform-methanol (95:5 V/V)
  8. additionwas treated with ether-ethyl acetate

출처 및 근거

ORD 기록
ord-90c6a3b9e7fa46c781833496bc0982aa
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727082

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