Sulfuric Acid → (S)-2-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester

HRID 1858385노트

반응식

HRID 1858385 반응식
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][OH:6].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:25]([N:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][OH:6])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 10855374(S)-Azetidin-2-ylmethanol

생성물 1

HCID 10900173(S)-2-Hydroxymethyl-azetidine-1-carboxylic acid benzyl ester수율 85%

실험 절차

This solution of (S)-azetidine-2-methanol was adjusted to pH 10 by adding 10% sulfuric acid, sodium hydrogen carbonate (2.00 g, 24.0 mmol) was then added, and benzyloxycarbonyl chloride (4.00 g, 24.0 mmol) was added thereto at room temperature. The mixture was then stirred for 14 hours. The solution was adjusted to pH 7, and extracted with ethyl acetate (50 mL×2). The extract was washed with water (50 mL×1), dried over magnesium sulfate and filtered, and the filtrate was concentrated. The concentrate was subjected to column chromatography (Wakogel C-200) using toluene/ethyl acetate (1/1) as a mobile phase. This separation/purification gave (S)-N-benzyloxycarbonylazetidine-2-methanol (1.88 g, yield 85.0%). The yield was improved as compared with that obtained in Example 1 (69.1%). The formation of the byproduct (S)-2-N-benzyloxycarbonyl-1,4-butanediol decreased to a yield of 3.0% (0.07 g).

후처리

  1. additionwas then added
  2. customat room temperature
  3. extractionextracted with ethyl acetate (50 mL×2)
  4. washThe extract was washed with water (50 mL×1)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThis separation/purification

출처 및 근거

ORD 기록
ord-3a5df932c75c4c50a62a2819e94b6d07
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150535

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