Water → (7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

HRID 331102노트

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HRID 331102 반응식
O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C-:17]#[N:18].[Na+].[C:20](=[O:23])([O-])[O-].[NH4+:24].[NH4+].[OH2:26]>C(O)C>[O:26]=[C:17]1[NH:24][C:20](=[O:23])[C:2]2([CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:3]2)[NH:18]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 86668857(R)-benzyl 3-oxocyclopentanecarboxylate

생성물 1

HCID 68179167(7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

To (R)-benzyl 3-oxocyclopentanecarboxylate (0.5 g, 2.291 mmol) in ethanol (5 mL) were sequentially added sodium cyanide (0.281 g, 5.73 mmol), ammonium carbonate (2.86 g, 29.8 mmol) and water (5.00 mL) at room temperature. The contents were heated at 70° C. (oil bath temp.) for 3 hours. The reaction mixture was kept at room temperature for 10 min. Solid separates out. The solid was filtered and washed with water (3×10 mL). The solid was dried overnight under vacuum (155 mg, 0.538 mmol, 23.5%) and used as such for the subsequent step without further purification. MS (ESI) m/z 289.16 (M+H)+

후처리

  1. customat room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water (3×10 mL)
  4. customThe solid was dried overnight under vacuum (155 mg, 0.538 mmol, 23.5%)
  5. customwithout further purification

출처 및 근거

ORD 기록
ord-24fdb3dcca614906b838a33b7cfb166d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877749B2

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