Sodium Bicarbonate → HCID 67526810, compound

HRID 133775Notes

Reaction equation

HRID 133775 reaction equation
[OH:1][C:2]([CH3:26])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:15])[CH:7]=1)=[O:4].COCCN(S(F)(F)[F:37])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:37][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:2]([OH:1])([CH3:26])[C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:15])[CH:7]=2)=[O:4])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67525756HCID 67525756, compound

Product 1

HCID 67526810HCID 67526810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 2-hydroxy-3-(4-hydroxymethylphenoxy)-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide (prepared in Example 70, 950 mg, 0.002636 mol) in dry CH2Cl2 (6.5 ml) was treated with Deoxo-Fluor® (875 mg, 0.003954 mol) in CH2Cl2 (3 ml) at −76° C. The solution was stirred at −10° C. for 3 hours. The saturated NaHCO3 solution was added and the mixture was extracted with dichloromethane. The combined extracts were washed with water, dried over Na2SO4, filtered, and evaporated in vacuo. The crude product was purified by flash chromatography using heptane/ethyl acetate as a gradient eluent (9:1-5:5). Crystallization from dichloromethane/heptane gave the desired compound. 1H NMR (400 MHz, DMSO-d6): 1.44 (3H, s), 2.53 (3H, s), 4.00 (1H, d, 2Jgem=9.7 Hz), 4.24 (1H, d, 2Jgem=9.6 Hz), 5.30 (2H, d, 2JHF=48.6 Hz), 6.21 (1H, s, —OH), 6.95 (2H, d, 3J=8.4 Hz), 7.34 (2H, d, 3J=8.6 Hz), 7.84 (1H, dd, 3J=9.0 Hz, 4J=2.0 Hz), 7.93 (1H, broad s), 8.03 (1H, d, 3J=9.0 Hz), 10.14 (1H, s, —NHCO—).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography
  7. customCrystallization from dichloromethane/heptane

Sources & evidence

ORD record
ord-9a019a702ebe40d296ccb2d7e25a06f4
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

Loading…