Sodium Hydroxide → 4-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid

HRID 80963Notes

Reaction equation

HRID 80963 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([N:14]2[CH2:19][CH2:18][C@:17]([CH2:26][C:27]([OH:30])([CH3:29])[CH3:28])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:16][C:15]2=[O:31])[CH3:13])=[CH:8][CH:7]=1>O1CCCC1>[OH:30][C:27]([CH3:28])([CH3:29])[CH2:26][C@@:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][C:15](=[O:31])[N:14]([C@H:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:32])=[O:4])=[CH:7][CH:8]=2)[CH3:13])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 581095974-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid methyl ester

Product 1

HCID 581092884-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M aqueous NaOH solution (5 mL) was added to a solution of 4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid methyl ester (0.73 g) in tetrahydrofuran (5 mL). The resulting solution was stirred at room temperature overnight. Then, the solution was concentrated and the residue was taken up in water and filtered. The aqueous filtrate was acidified with 1 M hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed to afford the title compound as a foam-like solid.

Workup

  1. concentrationThen, the solution was concentrated
  2. filtrationfiltered
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-88acb2894186450aa00722d0a9e566ac
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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