Sodium Hydroxide → HCID 69267825, compound

HRID 2055587Notes

Reaction equation

HRID 2055587 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([NH:17][C:18]([C:20]2([NH:23]C(=O)C(F)(F)F)[CH2:22][CH2:21]2)=[O:19])[CH3:16])=[C:11]([F:30])[CH:10]=1.[OH-].[Na+]>CO>[NH2:23][C:20]1([C:18]([NH:17][C@@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[NH2:1])=[CH:10][C:11]=2[F:30])[CH3:16])=[O:19])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86608821HCID 86608821, compound

Product 1

HCID 69267825HCID 69267825, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(1R)-1-(2′-amino-3,3′-difluoro-1,1′-biphenyl-4-yl)ethyl]-1-[(trifluoroacetyl)amino]cyclopropanecarboxamide (174 mg 0.407 mmol) in methanol (2 ml) was added 1.0N NaOH (2 ml, 2 mmol) and stirred at room temperature 4 days. This mixture was concentrated under vacuum to a 2 ml volume and extracted with methylene chloride (2×10 ml). The combined extracts were washed with water (1 ml), dried over MgSO4, filtered and the solvent removed in vacuo to give 1-amino-N-[(1R)-1-(2′-amino-3,3′-difluoro-1,1′-biphenyl-4-yl)ethyl]cyclopropanecarboxamide. Low resolution mass spectrometry: (M+H+)=332.3.

Workup

  1. concentrationThis mixture was concentrated under vacuum to a 2 ml volume
  2. extractionextracted with methylene chloride (2×10 ml)
  3. washThe combined extracts were washed with water (1 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9781e7ecdde34e2f906c38c30feeab65
Source dataset
uspto-grants-2008_02
Patent number
US07332499B2

Reaction notes

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