Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylate → 2-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl ester

HRID 29765Notes

Reaction equation

HRID 29765 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][PH:10](=[O:12])[OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([O:15][C:16](=[O:34])[C:17]([CH2:19][C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:24][CH:25]=1)=[CH2:18])[CH3:14]>CC#N>[CH2:13]([O:15][C:16](=[O:34])[CH:17]([CH2:19][C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[CH:24][CH:25]=1)[CH2:18][P:10]([OH:11])([CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12])[CH3:14]

Participants

4

Reactant 2

HCID 54494317Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylateHCID 178527054HCID 178527054, compound

Product 1

HCID 541967722-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl esterYield 45.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3-Phenyl-propyl)-phosphinic acid (0.579 g 3.143 mmol) and 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.327 g 1.067 mmol) in MeCN (7.5 mL) was degassed using the freeze-thaw technique. BSA (2.55 g 12.57 mmol) was added and the mixture was stirred for 3 days and concentrated under reduced pressure. The residue was dissolved in chloroform, washed with NaHCO3 and brine, dried and concentrated under reduced pressure. Flash chromatography (CH2Cl2/MeOH, 8:2) gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl ester (0.240 g, 16%).

Workup

  1. additionBSA (2.55 g 12.57 mmol) was added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with NaHCO3 and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01691e857ae147da98817726457188e2
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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