Sodium Methoxide → HCID 51356430, compound

HRID 1874621Notes

Reaction equation

HRID 1874621 reaction equation
C([O:4][CH2:5][C@@H:6]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([CH3:30])[CH2:27][CH2:28][CH3:29])=[CH:20][CH:19]=1)[NH:7][C:8](=[O:17])[C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])(=O)C.C[O-].[Na+]>CO>[OH:4][CH2:5][C@H:6]([NH:7][C:8](=[O:17])[C@H:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:10])[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH:26]([CH3:30])[CH2:27][CH2:28][CH3:29])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67086148(2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethyl acetate

Product 1

HCID 51356430HCID 51356430, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethyl acetate (358 mg, 0.870 mmol) in methanol (5 mL) at 0° C. was added sodium methoxide (14.0 mL, 7.00 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 20 min. Saturated aqueous NH4Cl (5 mL) was added and the methanol was removed on the rotovapor. The mixture was transferred to a separatory funnel containing saturated aqueous NH4Cl solution (20 mL). The aqueous layer was extracted with ethyl acetate (4×20 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (40%→75% ethyl acetate in hexanes; 25 g column) to afford (2S)-N-((1R)-2-hydroxy-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide (269 mg, 84% yield) as a colorless solid: 1H NMR (400 MHz, CDCl3) δ 7.29-7.36 (m, 2H), 7.22-7.29 (m, 3H), 6.94 (d, J=8.6 Hz, 2H), 6.76 (d, J=8.6 Hz, 2H), 6.01 (d, J=6.8 Hz, 1H), 4.89-4.97 (m, 1H), 3.76 (d, J=4.8 Hz, 2H), 3.71-3.75 (m, 1H), 3.59-3.68 (m, 2H), 2.46 (br. s., 1H), 1.84-1.95 (m, 1H), 1.50 (d, J=7.1 Hz, 3H), 1.25-1.48 (m, 3H), 1.13-1.22 (m, 1H), 0.97 (d, J=6.8 Hz, 3H), 0.90 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 370.2 [(M+H)+, calcd for C23H32NO3 370.2].

Workup

  1. customThe cooling bath was removed
  2. additionSaturated aqueous NH4Cl (5 mL) was added
  3. customthe methanol was removed on the rotovapor
  4. customThe mixture was transferred to a separatory funnel
  5. additioncontaining saturated aqueous NH4Cl solution (20 mL)
  6. extractionThe aqueous layer was extracted with ethyl acetate (4×20 mL)
  7. washThe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography on silica gel (40%→75% ethyl acetate in hexanes; 25 g column)

Sources & evidence

ORD record
ord-d54dc73e525f4a6db16017e69ffca56f
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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