Sodium Bicarbonate → HCID 67526944, compound

HRID 133774Notes

Reaction equation

HRID 133774 reaction equation
[OH:1][C:2]([CH3:27])([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]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:38])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:38][CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:2]([OH:1])([CH3:27])[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 67527293HCID 67527293, compound

Product 1

HCID 67526944HCID 67526944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-hydroxy-3-[4-(2-hydroxyethylphenoxy]-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide (prepared in Example 20, 300 mg, 0.0008012 mol) in dry CH2Cl2 (3 ml) was treated with Deoxo-Fluor® (195 mg, 0.0008813 mol) in dry CH2Cl2 (1 ml) at −15 to −10° C. The solution was stirred for 2 h at 0° C. and then for 3 days at room temperature. 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 dichloromethane as an eluent. Crystallization from toluene afforded the desired compound as pure crystals: m.p. 102-105° C. 1H NMR (400 MHz, DMSO-d6): 1.43 (3H, s), 2.53 (3H, s), 2.88 (2H, dt, 3JHF=24.4 Hz, 3J=6.4 Hz), 3.95 (1H, d, 2Jgem=9.8 Hz), 4.18 (1H, d, 2Jgem=9.5 Hz), 4.56 (2H, dt, 2JHF=47.4 Hz, 3J=6.4 Hz), 6.18 (1H, broad s, —OH), 6.85 (2H, d, 3J=8.5 Hz), 7.15 (2H, d, 3J=8.4 Hz), 7.88 (1H, d, 3J=9.0 Hz), 7.93 (1H, s), 8.03 (1H, d, 3J=9.0 Hz), 10.13 (1H, broad s, —NHCO—).

Workup

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

Sources & evidence

ORD record
ord-a9c981d683f24cdaaf02ceabcc8aa6ac
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

Loading…