N-Boc-4,4-difluoro-L-proline methyl ester → (2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 525001

반응식

HRID 525001 반응식
[F:1][C:2]1([F:18])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16]C)=[O:15])[CH2:3]1>CO.O1CCCC1.[OH-].[Na+]>[C:10]([O:9][C:7]([N:5]1[CH2:6][C:2]([F:1])([F:18])[CH2:3][C@H:4]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:13])([CH3:11])[CH3:12]

참가 물질

5

반응물 1

HCID 11129200N-Boc-4,4-difluoro-L-proline methyl ester

생성물 1

HCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid수율 99%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

1.08 g (4.08 mmol) of (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate (purchased from Aldrich®; cat. no. 702463) were dissolved in a mixture of 10 mL of methanol and 10 mL of tetrahydrofurane and 6.12 mL of a 2M aqueous solution of sodium hydroxide were added. The solution was stirred at room temperature for 1 hour and then the organic solvents were removed. The remaining solution was diluted with water and 6.12 mL of 2M hydrochloric acid were added. The product that precipitated was extracted with dichloromethane (×3), the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and the solvent was removed. 1.01 g (99% yield) of the title compound were obtained as a white solid.

후처리

  1. additionwere added
  2. customthe organic solvents were removed
  3. additionThe remaining solution was diluted with water and 6.12 mL of 2M hydrochloric acid
  4. additionwere added
  5. customThe product that precipitated
  6. extractionwas extracted with dichloromethane (×3)
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent was removed

출처 및 근거

ORD 기록
ord-429dd18a78c443ad8a13d8876b6badf6
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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