Sodium Hydroxide → Boc-Hyp(Bzl)-OH

HRID 525045노트

반응식

HRID 525045 반응식
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:21]([O:23]C)=[O:22])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C@H:11]([C:21]([OH:23])=[O:22])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 148639421-tert-Butyl 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

생성물 1

HCID 11860409Boc-Hyp(Bzl)-OH수율 76%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

(2S,4R)-1-tert-Butyl 2-methyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (2.78 g, 8.29 mmol) was dissolved in a 1:1 mixture of MeOH and THF (30 ml) and 2N NaOH (12.5 ml, 26 mmol) was added. After stirring at room temperature for 2 h, the organic solvents were evaporated under reduced pressure and the aqueous phase was extracted twice with dichloromethane. The aqueous phase was then cooled at 0° C. and then acidified with concentrated chlorhydric acid. This phase was extracted twice with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 2.01 g (76% yield) of the final compound were obtained, pure enough to perform the next synthetic step.

후처리

  1. additionwas added
  2. customthe organic solvents were evaporated under reduced pressure
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. temperatureThe aqueous phase was then cooled at 0° C.
  5. extractionThis phase was extracted twice with dichloromethane
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-2f7f63b0e972437ab6e50c0898cb9aa2
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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