Sodium hydride → 4-(4,4-Dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 433071노트

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HRID 433071 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][C:14](=[O:17])[NH:13][CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:18][O:19][CH:20]([O:25][CH3:26])[CH2:21][CH2:22][CH2:23]Br>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:16][CH2:15][C:14](=[O:17])[N:13]([CH2:23][CH2:22][CH2:21][CH:20]([O:25][CH3:26])[O:19][CH3:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 104202254-Bromo-1,1-dimethoxybutaneHCID 226177365-Oxo-(1,4)diazepane-1-carboxylic acid tert-butyl ester

생성물 1

HCID 692244834-(4,4-Dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester수율 51.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a suspension of 60% sodium hydride in mineral oil (0.2 g, 5 mmole) in N,N-dimethylformamide (6 mL) was added 5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.0 g, 4.67 mmole). The reaction mixture was warmed at 50° C. for 5 minutes, and then at room temperature for 15 minutes. To the resulting solution was added 4-bromobutyraldehyde dimethyl acetal (0.99 g, 5 mmole). After the reaction mixture was stirred at room temperature for 16 hours, the solvent was removed, and the residue was partitioned between water and ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate), and concentrated. The residue was dissolved in diethyl ether, and the suspension was filtered, and the filtrate was concentrated. Purification by silica gel chromatography, eluting with 2% methanol in chloroform, gave 4-(4,4-dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.8 g,) as a heavy syrup. Nmr: (chloroform-d) δ (ppm) 1.49, s, (9H); 2.64, m, 3H; 3.32, s (3H); 4.37, m, (1H).

후처리

  1. customthe solvent was removed
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in diethyl ether
  7. filtrationthe suspension was filtered
  8. concentrationthe filtrate was concentrated
  9. customPurification by silica gel chromatography
  10. washeluting with 2% methanol in chloroform

출처 및 근거

ORD 기록
ord-873d5258a3df42bb8ec939e21634a3a1
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667301B2

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