Hydrochloric Acid → HCID 54137898、化合物

HRID 620792

反応式

HRID 620792 の反応式
[Si: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]([CH2:21][OH:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:24][C:25]([OH:27])=[O:26].[OH-].[K+].[I-].[K+].Cl.[Cl-].[Na+]>C(O)(C)(C)C.O>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][C@H:11]1[CH2:21][O:22][CH2:24][C:25]([OH:27])=[O:26])=[O:15])([CH3:20])([CH3:19])[CH3:18]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

生成物 1

HCID 54137898HCID 54137898、化合物収率 78.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of (2S,4R)-4-t-butyldimethylsilyloxy-1-t-butoxycarbonyl-2-(hydroxymethyl)pyrrolidine (0.62 g), 2-bromoacetic acid (0.26 g), 85% potassium hydroxide (0.37 g), and potassium iodide (0.93 g) in t-butyl alcohol (12 ml) was heated at 50° C. for 3 hours. The mixture was poured into water (100 ml), adjusted to pH 4 with 1N hydrochloric acid and saturated with sodium chloride. The aqueous mixture was extracted with three 50 ml portions of ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (30 g ) eluting with a mixture of methanol and dichloromethane (1:9 V/V) to give (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(carboxymethyloxymethyl)pyrrolidine (0.57 g).

後処理

  1. extractionThe aqueous mixture was extracted with three 50 ml portions of ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (30 g )
  6. washeluting with a mixture of methanol and dichloromethane (1:9 V/V)

出典と根拠

ORDレコード
ord-cca902987ef84e6990b3784a70923176
出典データセット
uspto-grants-1989_04
特許番号
US04822787

関連ノート

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