3-Pyridinemethanol → HCID 54273281, compound

HRID 2165295Notes

Reaction equation

HRID 2165295 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][C@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:10])=[O:5])[CH3:2].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37]O)[CH:32]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@H:6]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:7][C@H:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH2:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1)=[O:15])=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 10868DicyclohexylcarbodiimideHCID 14557735HCID 14557735, compound

Product 1

HCID 54273281HCID 54273281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 2.37 g of N-[4-ethoxycarbonyl-(R*,R*)-2,4-dibenzylbutyryl]-3-aminopropionic acid, 0.61 g of 3-pyridylcarbinol and 1.15 g of dicyclohexylcarbodiimide in 25 ml of methylene chloride is stirred at room temperature for two days. The solid is removed, and the filtrate is diluted with 150 ml of ether and extracted with 0.5N hydrochloric acid. The acidic aqueous layer is separated, basified and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride, dried over magnesium sulfate, filtered, concentrated and flash chromatographed on silica gel eluting with ethyl acetate:ethanol (9:1) to yield 3-pyridylmethyl N-[4-ethoxycarbonyl-(R*,R*)-2,4-dibenzylbutyryl]-3-aminopropionate as an oil; NMR (CDCl3) δ 8.70 (m, 2H), 7.77 (m, 1H), 7.28 (m, 11H), 5.56 (t, 1H, J=7 Hz), 5.12 (s, 2H), 4.03 (q, 2H, J=8 Hz), 1.08 (t, 3H, J=8 Hz).

Workup

  1. customThe solid is removed
  2. additionthe filtrate is diluted with 150 ml of ether
  3. extractionextracted with 0.5N hydrochloric acid
  4. customThe acidic aqueous layer is separated
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customflash chromatographed on silica gel eluting with ethyl acetate:ethanol (9:1)

Sources & evidence

ORD record
ord-2485b7356940426cb9f0c74d290d88f8
Source dataset
uspto-grants-1990_07
Patent number
US04939261

Reaction notes

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