Hydrochloric Acid → HCID 54137898, 화합물

HRID 620792

반응식

HRID 620792 반응식
[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]

참가 물질

9

반응물 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

생성물 1

HCID 54137898HCID 54137898, 화합물수율 78.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cca902987ef84e6990b3784a70923176
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822787

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