Benzyl Bromide → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one

HRID 247704노트

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HRID 247704 반응식
[H-].[Na+].C([N:10]1[C@H:13](CCO)[C@@H:12]([C@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])[C:11]1=[O:27])C1C=CC=CC=1.C(Br)C1C=CC=CC=1>O.C1COCC1.CN(C)C=O>[Si:20]([O:19][C@@H:17]([C@@H:12]1[CH2:13][NH:10][C:11]1=[O:27])[CH3:18])([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21]

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 139595691-benzyl-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-4(R)-(2-hydroxyethyl)-2-azetidinone

생성물 1

HCID 10130795(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one수율 58%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

There were added 1 ml of THF and 0.6 ml of dimethylformamide to 13 mg (0.26 mmol) of sodium hydride (oiliness: 50%), to which 2 ml of a THF solution of 64 mg (0.18 mmol) of 1-benzyl-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-4(R)-(2-hydroxyethyl)-2-azetidinone on the ice bath and the mixture was stirred for 10 minutes. Thereto 0.03 ml (0.25 mmol) of benzyl bromide was added and the mixture was stirred at room temperature for a night. The reaction mixture was added with water, extracted three times with diethyl ether, and the obtained extract was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate and concentrated. The obtained residue was purified by 10 g of silica gel-column chromatography (eluent; hexane:diethyl ether=1:1) to give 46 mg of 1-benzyl-4(R)-2-benzyloxyethyl)-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-2-azetidinone (yield: 58%).

후처리

  1. extractionextracted three times with diethyl ether
  2. extractionthe obtained extract
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by 10 g of silica gel-column chromatography (eluent; hexane:diethyl ether=1:1)

출처 및 근거

ORD 기록
ord-5529d26c64614193a5c8a7a4375d5f6c
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709064

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