Sodium Carbonate → HCID 68849304, compound

HRID 730405Notes

Reaction equation

HRID 730405 reaction equation
C([SiH](CC)CC)C.[B].[CH2:9]([CH:16]1[CH2:20][O:19][C:18](=[O:21])[N:17]1[C:22](=[O:51])[CH:23]([O:48][CH2:49][CH3:50])[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](C)[C:40](=O)OC(C)(C)C)[CH:33]=2)=[CH:28][CH:27]=1)O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:9]([CH:16]1[CH2:20][O:19][C:18](=[O:21])[N:17]1[C:22](=[O:51])[CH:23]([O:48][CH2:49][CH3:50])[CH2:24][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][NH:39][CH3:40])[CH:33]=2)=[CH:28][CH:27]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 5462311BoronHCID 68849985HCID 68849985, compound

Product 1

HCID 68849304HCID 68849304, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

43 ml (272 mmol) of triethylsilane are added dropwise to a solution of 17 ml (136 mmol) of boron trifluoroetherate in 150 ml of dichloromethane cooled beforehand to 0° C. After stirring for 15 minutes, 10 g (17 mmol) of tert-butyl N-{4′-[3-(4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylcarbamate dissolved in 70 ml of dichloromethane are added dropwise. The reaction medium is stirred from 0° C. to room temperature for 3 hours and then heated at 40° C. for 48 hours, treated with saturated aqueous sodium carbonate solution, extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated. The residue obtained is purified by chromatography on a column of silica eluted with a dichloromethane/methanol/triethylamine mixture (95/5/0.5). 8 g of 4-benzyl-3-[2-ethoxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionyl]oxazolidin-2-one are obtained in a yield of 13% to 3 g of methyl 2-ethoxy-3-hydroxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionate are obtained in a yield of 51%.

Workup

  1. additionare added dropwise
  2. stirringThe reaction medium is stirred from 0° C. to room temperature for 3 hours
  3. temperatureheated at 40° C. for 48 hours
  4. extractionextracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with a dichloromethane/methanol/triethylamine mixture (95/5/0.5)

Sources & evidence

ORD record
ord-37c42291eede4f6dad8abeab7127ca40
Source dataset
uspto-grants-2009_09
Patent number
US07582663B2

Reaction notes

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