Sodium borohydride → HCID 57577369, 화합물

HRID 1921691노트

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HRID 1921691 반응식
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:36])[C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[C:14]1=[O:31])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:36])[C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[CH:14]1[OH:31])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 57577370Diethyl acetamido(6-octyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanedioate2회

생성물 1

HCID 57577369HCID 57577369, 화합물수율 75.6%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of sodium borohydride (75 mg, 2.00 mmol) in 5 ml of ethanol at room temperature is added 2-acetylamino-2-(6-octyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester (compound 5) (1.00 g, 2.1 mmol) in 5 ml of ethanol. The reaction mixture is stirred at room temperature under argon for an additional hour, quenched by the addition of water (20 mL) and methylene chloride (20 mL). The organic layer is removed and the aqueous layer is extracted with methylene chloride (2×20 mL). The combined organic layers were washed with brine (2×20 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 20% ethyl acetate in hexanes) to provide 755 mg of compound A (75%).

후처리

  1. customquenched by the addition of water (20 mL) and methylene chloride (20 mL)
  2. customThe organic layer is removed
  3. extractionthe aqueous layer is extracted with methylene chloride (2×20 mL)
  4. washThe combined organic layers were washed with brine (2×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by column chromatography (silica gel, 20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-32b0801000f94920870d7ca21932cfb3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173710B2

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