Trifluoroacetic acid → HCID 58010930, compound

HRID 2079418Notes

Reaction equation

HRID 2079418 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:28])[O:22][C@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:28])[O:22][C@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58010887HCID 58010887, compound

Product 1

HCID 58010930HCID 58010930, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of (S)-tetrahydrofuran-3-yl (R)-1-(tert-butoxycarbonyl)pyrrolidin-3-ylcarbamate (490 mg, 1.63 mmol) in 5 μL CH2Cl2. After stirring for 30 min, the reaction was quenched with NaOH and extracted twice with EtOAc. The organic extracts were combined, dried over MgSO4, filtered, and concentrated to yield (S)-tetrahydrofuran-3-yl (R)-pyrrolidin-3-ylcarbamate (230 mg) which was used without further purification. LC/MS: m/z 201.3 (M+H)+ at 0.59 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe reaction was quenched with NaOH
  2. extractionextracted twice with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d4aabb34a79f4e7abf53e2ef7fde435f
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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