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Sodium hydride → Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 2362943
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HRID 2362943 반응식
[H-].[Na+].[CH:3]1([N:9]2[C:13]3([CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:14]3)[C:12](=[O:29])[NH:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:31][C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>CN(C)C=O.O>[C:38]([O:37][C:35]([C:34]1[CH:33]=[C:32]([CH:44]=[CH:43][CH:42]=1)[CH2:31][N:11]1[C:12](=[O:29])[C:13]2([CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[CH2:15][CH2:14]2)[N:9]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:10]1)=[O:36])([CH3:41])([CH3:39])[CH3:40]
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6

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HCID 24758Sodium hydrideHCID 14591193tert-Butyl 3-(bromomethyl)benzoateHCID 58046657Benzyl 1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

생성물 1

HCID 58046810Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate수율 88%

시약·촉매·용매 2

HCID 962Water
용매
HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

Sodium hydride (0.0699 g, 2.91 mol) was added portionwise at 0° C. to benzyl 1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.03 g, 2.77 mmol) in N,N-dimethylformamide (5 mL) and stirred at 0° C. for 10 minutes. tert-Butyl 3-(bromomethyl)benzoate (0.75 g, 2.77 mmol) was added dropwise at 0° C., the mixture allowed to warm to room temperature, and stirred overnight. The reaction was diluted with water and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by PTLC (50% ethyl acetate/hexanes) to give product as an oil (1.37 g, 88%); 1H NMR (DMSO-d6); δ0.97 (m, 1H); 1.20 (m, 4H); 1.53 (s, 9H); 1.53-1.69 (m, 9H); 2.60 (m, 1H); 3.59 (m, 2H); 3.73 (m, 2H); 4.47 (s, 2H); 5.09 (s, 2H); 7.30-7.39 (m, 5H); 7.45-7.50 (m, 2H); 7.73 (m, 1H); 7.81 (m, 1H); MS for C33H43N3O5 m/z 562 (M+H)+.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by PTLC (50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-3da44df7f08843c880ed951c42ed7c76
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691836B2

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