(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 4670Notes

Reaction equation

HRID 4670 reaction equation
[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]

Participants

4

Reactant 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

Product 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 saltYield 42.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-90c6a3b9e7fa46c781833496bc0982aa
Source dataset
uspto-grants-1988_02
Patent number
US04727082

Reaction notes

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