Sodium Hydroxide → Boc-Hyp(Bzl)-OH

HRID 525045ノート

反応式

HRID 525045 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 11860409Boc-Hyp(Bzl)-OH収率 76%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-2f7f63b0e972437ab6e50c0898cb9aa2
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

反応ノート

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