Acetic Acid → HCID 86669247, 화합물

HRID 2366909노트

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HRID 2366909 반응식
[CH3:1][CH:2]([O:4][C:5](=[O:28])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[O:18][CH:19]=[C:20]([CH:22]=O)[CH:21]=3)[CH:15]=2)[N:10]([C:24](=[O:26])[CH3:25])[C@@H:9]([CH3:27])[CH2:8]1)[CH3:3].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:24]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[O:18][CH:19]=[C:20]([CH2:22][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:21]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:28])[O:4][CH:2]([CH3:3])[CH3:1])[CH2:8][C@@H:9]1[CH3:27])(=[O:26])[CH3:25]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86669230HCID 86669230, 화합물

생성물 1

HCID 86669247HCID 86669247, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-Methylethyl[(cis)-1-acetyl-6-(4-formyl-2-furanyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 20) (28 mg, 0.073 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with piperidine (8.65 μL, 0.087 mmol) and acetic acid (8.34 μL, 0.146 mmol) and stirred under nitrogen for 30 minutes. Sodium triacetoxyborohydride (20.07 mg, 0.095 mmol) was added and the mixture was stirred again under nitrogen. After 16 hours reaction time the mixture was loaded onto a 2 g Flash SCX-column, eluting with MeOH (60 mL) followed by 2M MeOH/NH3 (60 mL). The product-containing fraction was evaporated to dryness to give a light brown solid (19 mg).

후처리

  1. stirringthe mixture was stirred again under nitrogen
  2. customAfter 16 hours reaction time the mixture
  3. washeluting with MeOH (60 mL)
  4. customThe product-containing fraction was evaporated to dryness

출처 및 근거

ORD 기록
ord-9262b3e6abe44d3aa6f921bab622d71b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697725B2

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