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Triethylamine → 4-Fluoro-L-proline

HRID 557112
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HRID 557112 반응식
[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
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11430Potassium Carbonate2회HCID 17607Sulfuryl fluoride

생성물 1

HCID 222148884-Fluoro-L-proline

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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,

후처리

  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

출처 및 근거

ORD 기록
ord-c1b4b1885cbc441a8ce03ccc5ebb84de
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08058412B2

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