Lithium Hydroxide → 3-[(tert-Butoxycarbonyl)amino]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid

HRID 592053Notes

Reaction equation

HRID 592053 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]2[O:15][C@@H:11]([CH2:12][CH2:13]2)[C@@H:10]1[C:16]([O:18]C)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO.O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:14]2[O:15][CH:11]([CH2:12][CH2:13]2)[CH:10]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89738587HCID 89738587, compound

Product 1

HCID 170393533-[(tert-Butoxycarbonyl)amino]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

(1S,2R,3S,4R)-methyl 3-(tert-butoxycarbonylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxylate (12) (600 mg, 2.2 mmol) was taken in MeOH/H2O (3:1) and LiOH (265 mg, 11 mmol) was added at 0° C. The reaction mixture was allowed to come to rt and then stirred at rt for 16 h. MeOH was removed and saturated ammonium chloride solution was added. This was followed by extraction with DCM. The aqueous extract was acidified to pH 3 using 1N HCl and extracted with DCM again. The combined organic extracts was dried and concentrated to afford the desired product (450 mg, 87%) as an off white solid.

Workup

  1. customto come to rt
  2. customMeOH was removed
  3. additionsaturated ammonium chloride solution was added
  4. extractionThis was followed by extraction with DCM
  5. extractionThe aqueous extract
  6. extractionextracted with DCM again
  7. customThe combined organic extracts was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3ec162dfd0414d08beea9f2239133ea9
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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