Water → HCID 69366184, 화합물

HRID 397323노트

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HRID 397323 반응식
[H-].[Na+].[C:3]([O:7][C:8](=[O:26])[NH:9][C@@H:10]([CH3:25])[CH2:11][C:12]1[C:20]2[CH:19]=[C:18]([OH:21])[CH:17]=[CH:16][C:15]=2[N:14]2[CH2:22][CH2:23][CH2:24][C:13]=12)([CH3:6])([CH3:5])[CH3:4].[CH3:27][O:28][C:29](=[O:32])[CH2:30]Br.O>CS(C)=O.C(OCC)(=O)C>[CH3:27][O:28][C:29](=[O:32])[CH2:30][O:21][C:18]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:22][CH2:23][CH2:24][C:13]3=[C:12]([CH2:11][C@@H:10]([NH:9][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:26])[CH3:25])[C:20]=2[CH:19]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 69364305HCID 69364305, 화합물

생성물 1

HCID 69366184HCID 69366184, 화합물수율 89.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

0.42 g sodium hydride 55-65% in oil was added to a solution of 3.3 g (S)-[2-(6-hydroxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-8-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester in 30 mL dimethylsulfoxide and the mixture stirred at room temperature for 30 min. 1.68 g bromoacetic acid methyl ester was added to the resulting solution and the mixture stirred at room temperature for 2 h. The mixture was distributed between water and ethyl acetate. The phases separated and the organic phase was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. The residue crystallised under hexane and was dried to constant weight to yield 3.61 g of (S)-[8-(2-tert-butoxycarbonylamino-propyl)-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-6-yloxy]-acetic acid methyl ester as off white crystals melting at 87-88° C.

후처리

  1. stirringthe mixture stirred at room temperature for 2 h
  2. customThe phases separated
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue crystallised under hexane
  7. customwas dried to constant weight

출처 및 근거

ORD 기록
ord-179b7839532f4c1d96359418984a9368
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610685B2

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