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 2037822Notes

Reaction equation

HRID 2037822 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-8ee150ff73dd4952b668b44f57539f72
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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