Hydrochloric Acid → 1-[6-(4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]ethyl}-phenyl)-pyridazin-3-yl]-cyclopropanecarboxylic acid

HRID 1528623Notes

Reaction equation

HRID 1528623 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1([C:11]2[N:12]=[N:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([N:25]4[CH2:30][CH2:29][C:28]([CH2:37][C:38]([OH:41])([CH3:40])[CH3:39])([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[O:27][C:26]4=[O:42])[CH3:24])=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])C.Cl>CO>[OH:41][C:38]([CH3:39])([CH3:40])[CH2:37][C@@:28]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C:26](=[O:42])[N:25]([C@H:23]([C:20]2[CH:19]=[CH:18][C:17]([C:14]3[N:13]=[N:12][C:11]([C:8]4([C:6]([OH:7])=[O:5])[CH2:10][CH2:9]4)=[CH:16][CH:15]=3)=[CH:22][CH:21]=2)[CH3:24])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67997654HCID 67997654, compound

Product 1

HCID 679984231-[6-(4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]ethyl}-phenyl)-pyridazin-3-yl]-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M aqueous NaOH solution (1.5 mL) was added to a solution of 1-[6-(4-{1-[6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-pyridazin-3-yl]-cyclopropanecarboxylic acid ethyl ester (0.81 g) in methanol (5 mL) at room temperature. The solution was stirred at room temperature for 2 h and was then neutralized with 1 M aqueous hydrochloric acid. Most of the methanol was evaporated, the residue was diluted with water, and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), and concentrated to give the title compound as a solid. Yield: 0.72 g (93% of theory); LC (method 1): tR=1.44 min; Mass spectrum (ESI+): m/z=516 [M+H]+.

Workup

  1. customMost of the methanol was evaporated
  2. additionthe residue was diluted with water
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ebec6f7b2bcb4c98b3c3c36741f9412c
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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