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Triethylamine → 4-Fluoro-L-proline

HRID 557112
Notes
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Reaction equation

HRID 557112 reaction equation
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].S(F)([F:11])(=O)=O.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>C(#N)C>[F:11][CH:5]1[CH2:4][NH:3][C@H:1]([C:13]([OH:14])=[O:16])[CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium Carbonate2×HCID 17607Sulfuryl fluoride

Product 1

HCID 222148884-Fluoro-L-proline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.0 mL of acetonitrile, and 1.10 g (10.87 mmol, 1.09 eq) of triethylamine, followed by lowering the inside temperature to −40° C. and then bubbling 2.00 g (19.60 mmol, 1.96 eq) of sulfuryl fluoride from a cylinder. The inside temperature was returned to room temperature, and stirring was conducted for 20 hours and 20 minutes. Conversion of the reaction was found by gas chromatography measurement to be 100%. The reaction-terminated liquid was poured into a potassium carbonate aqueous solution [prepared from 2.80 g (20.26 mmol, 2.03 eq) of potassium carbonate and 50.0 mL of water], followed by extraction two times with 50.0 mL of ethyl acetate. The recovered organic layer was concentrated under reduced pressure, followed by vacuum drying, thereby obtaining a crude product of 4-fluoroproline derivative represented by the following formula,

Workup

  1. customto −40° C.
  2. customwas returned to room temperature
  3. extractionfollowed by extraction two times with 50.0 mL of ethyl acetate
  4. concentrationThe recovered organic layer was concentrated under reduced pressure
  5. customdrying

Sources & evidence

ORD record
ord-c1b4b1885cbc441a8ce03ccc5ebb84de
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08058412B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes