Sodium Hydroxide → HCID 67088600, compound

HRID 2081131Notes

Reaction equation

HRID 2081131 reaction equation
CC(C)(C)[C@H](NC1C=CC=C(C(F)(F)F)C=1)C([N:6]1[CH2:11][C@H:10]2[C@H:8]([C:9]2([CH3:13])[CH3:12])[C@H:7]1[C:14]([O:16]C)=[O:15])=O.[OH-].[Na+]>C1COCC1>[CH3:12][C:9]1([CH3:13])[CH:8]2[CH:10]1[CH2:11][NH:6][CH:7]2[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57988354HCID 57988354, compound

Product 1

HCID 67088600HCID 67088600, compoundYield 251.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R,2S,5S)-methyl 3-((S)-3,3-dimethyl-2-(3-(trifluoromethyl)phenylamino)butanoyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate (0.047 g, 0.11 mmol) in THF (1 mL) was added 0.4 N NaOH solution (0.69 mL, 0.28 mmol) and the reaction was stirred at rt for 3 hrs. THF was removed and acidified with saturated KHSO4 until PH=3˜4. The mixture was extracted with Ether (15 mL), washed with brine and dried over sodium sulfate. After removal of solvent, it gave the (1R,2S,5S)-3-((S)-3,3-dimethyl-2-(3-trifluoromethyl)phenylamino)butanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (0.043 g, 95%) as white solid. MS: Calcd.: 412; Found: [M−H]+ 411.

Workup

  1. customTHF was removed
  2. extractionThe mixture was extracted with Ether (15 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of solvent, it

Sources & evidence

ORD record
ord-8255d339ace84cab8066fb3607ea3ad4
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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