Sulfuric Acid → Pregabalin

HRID 269411

반응식

HRID 269411 반응식
S(=O)(=O)(O)O.COC(=O)[NH:9][CH2:10][C@H:11]([CH2:16][C:17](=[O:27])N[C@H](C1C=CC=CC=1)C)[CH2:12][CH:13]([CH3:15])[CH3:14].[OH-:29].[Na+]>>[CH3:15][CH:13]([CH2:12][C@H:11]([CH2:10][NH2:9])[CH2:16][C:17]([OH:27])=[O:29])[CH3:14]

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 59832562Methyl ((S)-4-Methyl-2-[2-oxo-2-[[(S)-1-phenylethyl]amino]ethyl]pentyl]carbamate

생성물 1

HCID 5486971Pregabalin수율 40.4%

반응 조건

온도
117.5 °C

실험 절차

A 0.2 l reactor was loaded with 70% sulfuric acid (200 g) containing compound 26 (10 g, 0.031 mole), and was heated to 115-120° C. for 5-10 hours, and then cooled to room temperature, i.e., about 20° to about 25° C. An aqueous 40% sodium hydroxide solution was added in an amount sufficient to provide a pH of 1. The solution was then extracted with 35 ml of iso-butanol, the organic layer was separated, and Bu3N was added in an amount sufficient to provide a pH of 4. The (S)-Pregabalin was precipitated, filtered, and washed with 10 ml of iso-butanol. After drying at 55° C. under vacuum, (S)-Pregabalin was obtained as white crystals in a 40.4% yield. Purity: 99.95% area by HPLC.

후처리

  1. temperaturecooled to room temperature
  2. customi.e., about 20° to about 25° C
  3. customto provide a pH of 1
  4. extractionThe solution was then extracted with 35 ml of iso-butanol
  5. customthe organic layer was separated
  6. additionBu3N was added in an amount sufficient
  7. customto provide a pH of 4
  8. customThe (S)-Pregabalin was precipitated
  9. filtrationfiltered
  10. washwashed with 10 ml of iso-butanol
  11. customAfter drying at 55° C. under vacuum

출처 및 근거

ORD 기록
ord-89f6577b588649f29e7cb0540f84b0c8
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446220B2

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