Sodium Bicarbonate → HCID 86651670, compound

HRID 337593Notes

Reaction equation

HRID 337593 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][NH:13][C:14](=[O:17])[CH2:15][CH3:16])[CH:5]=[C:6]([CH2:9][OH:10])[C:7]=1[Cl:8].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][NH:13][C:14](=[O:17])[CH2:15][CH3:16])[CH:5]=[C:6]([CH:9]=[O:10])[C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67061947HCID 67061947, compound

Product 1

HCID 86651670HCID 86651670, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-{2-[3,4-dichloro-5-(hydroxymethyl)phenyl]ethyl}propanamide (1 eq.) from the previous step and sodium bicarbonate (1.1 eq.) in dichloromethane (0.1 M) was added DMP (1.1 eq.) at 0° C. The resulting mixture was stirred at RT for 2 h before it was quenched with sat. aq. NaHSO3 and then extracted with Et2O. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a white solid.

Workup

  1. additionwas added DMP (1.1 eq.) at 0° C
  2. customwas quenched with sat. aq. NaHSO3
  3. extractionextracted with Et2O
  4. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-3fc7db367fa646179fc0ea6836abf51b
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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