Sodium Hydroxide → HCID 22983872, compound

HRID 1263480Notes

Reaction equation

HRID 1263480 reaction equation
[N+:1]([C:4]1[C:5]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]1=[O:22])([O-])=O.[OH-].[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+]>CC(C)=O.O>[NH2:1][C:4]1[C:5]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]1=[O:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 22983876HCID 22983876, compound

Product 1

HCID 22983872HCID 22983872, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a refluxing solution of compound 94 (506 mg, 1.35 mmol) in acetone (120 mL), H2O (24 mL) and aqueous 1 M NaOH (24 mL, 24.0 mmol) was portionwise added with care solid Na2S2O4 (3.89 g, 18.97 mmol). The reflux was continued for 2 h then the acetone was removed under vacuum. More H2O (50 mL) was added and the aqueous phase was extracted with CH2Cl2 (4×). The organic phase was dried (MgSO4), filtered then rotary evaporated. The crude solid was purified by flash chromatography (SiO2) using 3:7 to 1:1 EtOAc/Hexanes as eluent to give compound 95 (228 mg, 49%) as a foamy solid. 1H NMR (CDCl3) δ 0.88 (3H, s), 1.37-2.78 (14H, m), 3.41 (3H, s), 3.71 (2H, t, J=5.0 Hz), 4.09 (2H, 2.9 Hz), 6.52 (1H, s), 6.65 (1H, s).

Workup

  1. customthe acetone was removed under vacuum
  2. additionMore H2O (50 mL) was added
  3. extractionthe aqueous phase was extracted with CH2Cl2 (4×)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customThe crude solid was purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-b1345df5f8344a01825f4fa7bfc3460a
Source dataset
uspto-grants-2003_04
Patent number
US06541463B1

Reaction notes

Loading…