Sodium Hydroxide → HCID 86659562, compound

HRID 1431020Notes

Reaction equation

HRID 1431020 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[C:8]([S:10][C:11]2[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=2)[CH:7]=[C:6]([O:17][C:18]2[CH:23]=[CH:22][C:21]([P:24]([O:30][CH:31]([CH3:33])[CH3:32])([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])=[CH:20][CH:19]=2)[CH:5]=1.O1CCOCC1.[OH-].[Na+]>O>[CH:27]([O:26][P:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([S:10][C:11]3[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=3)[CH:7]=2)[C:3]([OH:34])=[O:2])=[CH:19][CH:20]=1)([O:30][CH:31]([CH3:33])[CH3:32])=[O:25])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 58529005HCID 58529005, compound

Product 1

HCID 86659562HCID 86659562, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-[4-(diisopropoxy-phosphoryl)-phenoxy]-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzoic acid methyl ester (292 mg, 0.58 mmol), 3 mL of dioxane, 3 mL of water and 1.2 mL of 1 M aqueous NaOH was stirred for 2 h at rt, diluted with water, washed with EtOAc, the aqueous layer pH lowered to 4 with 1 M NaHSO4, the aqueous layer extracted with 4:1 CH2Cl2/MeOH. The organic extract dried (MgSO4) and evaporated to provide 234 mg (82%) of the title compound: 1H NMR (500 MHz, DMSO-d6): δ 1.18 (d, 6H, J=6 Hz), 1.28 (d, 6H, J=6 Hz), 3.64 (s, 3H), 4.55 (m, 2H), 7.03 (t, 1H, J=2 Hz), 7.13 (s, 1H). 7.15 (dd, 2H, J=8, 3 Hz), 7.31 (dd, 1H, J=2, 1 Hz), 7.35 (t, 1H, J=1 Hz), 7.50 (s, 1H), 7.72 (dd, 2H, J=12, 8 Hz); LCMS (m/z): 491.9 [C23H27N2O6PS+H]+.

Workup

  1. washwashed with EtOAc
  2. extractionthe aqueous layer extracted with 4:1 CH2Cl2/MeOH
  3. extractionThe organic extract
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c8c5f8247d134f57b36267993dd637a9
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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