Hydrochloric Acid → 209860-88-8

HRID 517397Notes

Reaction equation

HRID 517397 reaction equation
C1(C2C=CC(C(O[C@@H:14]3[CH2:27][C@@H]4[O:18][C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH2:25][C@@H:16]4[C@H:15]3/[CH:28]=[CH:29]/[C:30]([F:40])([F:39])[CH2:31][O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=O)=CC=2)C=CC=CC=1.[OH-:43].[Na+].Cl.[CH3:46][OH:47]>C1COCC1>[F:39][C:30]([F:40])([CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)/[CH:29]=[CH:28]/[C@H:15]1[C@H:14]([OH:43])[CH2:27][C@H:46]([OH:47])[C@@H:16]1[CH2:25]/[CH:24]=[CH:23]\[CH2:22][CH2:21][CH2:20][C:19]([OH:26])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 117873680HCID 117873680, compound

Product 1

HCID 9978917209860-88-8

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6Z,8aR,9R,10R,11aS)-9-((E)-3,3-difluoro-4-phenoxybut-1-enyl)-2,3,4,5,8,8a,9,10,11,11a-decahydro-2-oxocyclopenta[b]oxecin-10-yl 4-phenylbenzoate (10.0 g from Example 35) in methanol (60 mL) and THF (160 mL) was treated with 3N sodium hydroxide aqueous solution (80 mL). This mixture was stirred at room temperature under an atmosphere of nitrogen for 2 hr. The reaction mixture was further adjusted to a pH of 8.5±0.2 with 3N hydrochloric acid aqueous solution and most of solvent was removed under reduced pressure. The residue was diluted with saturated aqueous solution of sodium bicarbonate (200 mL) and ethyl acetate (200 mL). The mixture was stirred at room temperatures for 5 minutes. The organic phase and the aqueous phase were separately collected. The aqueous layer was adjusted to a pH of 3.0±0.2 with 3N hydrochloric acid aqueous solution at room temperature and extracted with ethyl acetate (200 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 12 g of crude Tafluprost acid.

Workup

  1. customwas removed under reduced pressure
  2. additionThe residue was diluted with saturated aqueous solution of sodium bicarbonate (200 mL) and ethyl acetate (200 mL)
  3. stirringThe mixture was stirred at room temperatures for 5 minutes
  4. customThe organic phase and the aqueous phase were separately collected
  5. customwas adjusted to a pH of 3.0±0.2 with 3N hydrochloric acid aqueous solution at room temperature
  6. extractionextracted with ethyl acetate (200 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6530b024f32943fe9944889b4bd7a0b9
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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