Methanol → HCID 57389078, compound

HRID 1360332Notes

Reaction equation

HRID 1360332 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[C:9]([NH:10]C(OC)=O)=[CH:8][C:7]([O:15][CH3:16])=[CH:6][C:5]=1[CH2:17][CH3:18].CO.[OH-].[Li+]>O.C1COCC1>[NH2:10][C:9]1[CH:8]=[C:7]([O:15][CH3:16])[CH:6]=[C:5]([CH2:17][CH3:18])[C:4]=1[C:3]([OH:19])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59756047HCID 59756047, compound

Product 1

HCID 57389078HCID 57389078, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound O (21.9 g, 82.0 mmol) in H2O, THF, and MeOH (3:1:1, 255 mL) was treated with lithium hydroxide (9.80 g, 410 mmol) at 100° C. for 2 hours under N2. The reaction mixture was partially concentrated and the remaining aqueous phase was washed with dichloromethane (50 mL). The aqueous phase was acidified to pH 4-5 with 3 N HCl and then extracted with ethyl acetate (3×400 mL). The combined organic solutions were washed with saturated NaCl solution and dried over anhydrous Na2SO4. Filtration and concentration by rotary evaporation provided compound R (15.71 g, 98%) as an off-white powder. 1H NMR (CDCl3, 400 MHz) δ: 6.18 (d, 1H, J=2.0 Hz), 6.01 (d, 1H, J=2.0 Hz), 3.79 (s, 3H), 2.93 (q, 2H, J=7.0 Hz), 1.23 (t, 3H, J=7.5 Hz). ESMS m/z: 196.0 [M+H]+, 178.0 [M−OH]+.

Workup

  1. concentrationThe reaction mixture was partially concentrated
  2. washthe remaining aqueous phase was washed with dichloromethane (50 mL)
  3. extractionextracted with ethyl acetate (3×400 mL)
  4. washThe combined organic solutions were washed with saturated NaCl solution
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationFiltration and concentration
  7. customby rotary evaporation

Sources & evidence

ORD record
ord-fb158c9dea7f415ea266ffa3f9a47473
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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