Sulfuric Acid → (2R)-5,5,5-Trifluoro-2-hydroxypentanoic acid

HRID 714234

반응식

HRID 714234 반응식
N[C@H:2]([CH2:6][CH2:7][C:8]([F:11])([F:10])[F:9])[C:3]([OH:5])=[O:4].[OH:12]S(O)(=O)=O.N([O-])=O.[Na+]>O.CCOCC>[F:9][C:8]([F:11])([F:10])[CH2:7][CH2:6][C@@H:2]([OH:12])[C:3]([OH:5])=[O:4]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 7177181(R)-2-Amino-5,5,5-trifluoropentanoic acidHCID 23668193Sodium Nitrite

생성물 1

HCID 90080122(2R)-5,5,5-Trifluoro-2-hydroxypentanoic acid

시약·촉매·용매 2

HCID 962Water용매2회HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

To a cool (0° C.), stirred solution of (2R)-2-amino-5,5,5-trifluoropentanoic acid (4.09 g, 23.90 mmol) (U.S. Pat. No. 2009/0111858 A1) and H2SO4 (2.8 mL, 52.5 mmol) in water (95 mL) was added a solution of sodium nitrite (9.89 g, 143 mmol) in water (30 mL) dropwise via addition funnel over 60 min. The reaction mixture was allowed to slowly warm to room temperature and stirred overnight. The reaction mixture was diluted with Et2O, the aqueous phase was separated and extracted with Et2O (3×). The combined organics were dried (Na2SO4), filtered and concentrated under reduced pressure to provide Intermediate S-3A (4.1551 g, >99%) as an amber oil: 1H NMR (400 MHz, CDCl3) δ ppm 4.33 (1H, dd, J=8.03, 4.27 Hz), 2.09-2.42 (3H, m), 1.88-2.02 (1H, m).

후처리

  1. additiondropwise via addition funnel over 60 min
  2. temperatureto slowly warm to room temperature
  3. customthe aqueous phase was separated
  4. extractionextracted with Et2O (3×)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide Intermediate S-3A (4.1551 g, >99%) as an amber oil

출처 및 근거

ORD 기록
ord-84d73495319e4ff8ae8cadf41ffc8603
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187434B2

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