Sodium Hydroxide → HCID 86614205, compound

HRID 888078Notes

Reaction equation

HRID 888078 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])=O)(C)(C)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[N+:21]([C:19]1[CH:18]=[CH:17][C:16]([C:24]([F:30])([F:29])[C:25]([F:26])([F:27])[F:28])=[C:15]([CH:20]=1)[O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 86614206HCID 86614206, compound

Product 1

HCID 86614205HCID 86614205, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (S)-2-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in CH2Cl2 (5 mL), TFA (2.5 mL) was added and stirred at RT for 1 h. The mixture was diluted with CH2Cl2 (20 mL) and neutralized with sat NaHCO3 and then 2N NaOH. The mixture was transferred to a seperatory funnel and the layers separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried with MgSO4, filtered and concentrated in vacuo to yield the title compound as a yellow solid.

Workup

  1. customThe mixture was transferred to a seperatory funnel
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd45d5be9d1f4f09aa2feb7dad44e829
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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