Acetic Acid → HCID 70570873, compound

HRID 2403581Notes

Reaction equation

HRID 2403581 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:39]([CH3:51])[C:40](=[O:50])[CH2:41][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH:33]=2)=[CH:28][CH:27]=1)=O>C(Cl)(Cl)Cl.ClCCl>[OH:5][CH2:4][CH2:3][N:2]([CH2:24][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:39]([CH3:51])[C:40](=[O:50])[CH2:41][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:46])[CH3:47])[CH:33]=2)=[CH:28][CH:27]=1)[CH3:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 80162-(Methylamino)ethanolHCID 5049666Sodium triacetoxyborohydrideHCID 86667970HCID 86667970, compound

Product 1

HCID 70570873HCID 70570873, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(methylamino)ethanol (41 mg), sodium triacetoxyborohydride (166 mg), acetic acid (9 mg), and dichloromethane (4 ml) was added tert-butyl (2-{[(4′-formylbiphenyl-3-yl)methyl](methyl)amino}-2-oxoethyl)carbamate (200 mg), followed by stirring for 5 hours. To the reaction mixture was added CHCl3-saturated aqueous sodium hydrogen carbonate solution, the organic layer was dried over Na2SO4, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (3% MeOH/chloroform) to obtain tert-butyl (2-{[(4′-{[(2-hydroxyethyl)(methyl)amino]methyl}biphenyl-3-yl)methyl](methyl)amino}-2-oxoethyl)carbamate (230 mg) as a colorless oil.

Workup

  1. dry with materialthe organic layer was dried over Na2SO4
  2. customthe solvent was evaporated
  3. customThe obtained residue was purified by silica gel column chromatography (3% MeOH/chloroform)

Sources & evidence

ORD record
ord-3d595df131994fd3a68813ed8e3daa21
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

Loading…