Cesium carbonate → 1-((4S,5R)-5-(4-(6-(2-oxa-5-azaspiro[3.4]octan-5-ylmethyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-3-yl)-2,2-difluoroethanone

HRID 1487571노트

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HRID 1487571 반응식
[CH2:1]1[C:4]2([CH2:8][CH2:7][CH2:6][NH:5]2)[CH2:3][O:2]1.Cl[CH2:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C@H:23]3[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:34])[CH:31]([F:33])[F:32])[C@@H:24]3[CH2:35][F:36])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:3]1[C:4]2([CH2:8][CH2:7][CH2:6][N:5]2[CH2:10][C:11]2[N:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C@H:23]4[O:27][C:26]([CH3:29])([CH3:28])[N:25]([C:30](=[O:34])[CH:31]([F:33])[F:32])[C@@H:24]4[CH2:35][F:36])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:1][O:2]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 547591262-Oxa-5-azaspiro(3.4)octaneHCID 866955331-{(4S,5R)-5-[4-(6-Chloromethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone

생성물 1

HCID 866955341-((4S,5R)-5-(4-(6-(2-oxa-5-azaspiro[3.4]octan-5-ylmethyl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-3-yl)-2,2-difluoroethanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
55 °C

실험 절차

A mixture of 2-oxa-5-azaspiro[3.4]octane (0.1 mmol, 15.8 mg), 1-{(4S,5R)-5-[4-(6-Chloromethyl-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidin-3-yl}-2,2-difluoro-ethanone (Example 99, Step 2, 0.09 mmol, 37 mg) and cesium carbonate (0.25 mmol, 81 mg) and acetonitrile (1 mL) was heated to 55° C. for 5 hours. The crude mixture was filtered on a bed of celite and the cake was washed with CH2Cl2 (2 mL). The volatiles were removed. The crude mixtures were used “as is” in step 2.

후처리

  1. filtrationThe crude mixture was filtered on a bed of celite
  2. washthe cake was washed with CH2Cl2 (2 mL)
  3. customThe volatiles were removed

출처 및 근거

ORD 기록
ord-a3308aab0f354aeab067d0c9aad3684f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428528B2

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