Cesium carbonate → HCID 86689026, 화합물

HRID 40525

반응식

HRID 40525 반응식
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([C@@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])=[CH:8][CH:7]=2)[CH2:3]1.CS(Cl)(=O)=O.[F:23][C:24]1[C:29]([F:30])=[C:28]([CH3:31])[CH:27]=[CH:26][C:25]=1O.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CC(N(C)C)=O.O>[F:23][C:24]1[C:29]([F:30])=[C:28]([CH3:31])[CH:27]=[CH:26][C:25]=1[O:1][CH:2]1[CH2:3][N:4]([C:6]2[CH:7]=[CH:8][C:9]([C@@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])=[CH:10][CH:11]=2)[CH2:5]1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 27741512,3-Difluoro-4-methylphenolHCID 86689005(S)-N-{1-[4-(3-Hydroxy-azetidin-1-yl)-phenyl]ethyl}-acetamide

생성물 1

HCID 86689026HCID 86689026, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 31374Dimethylacetamide용매

반응 조건

온도
0 °C

실험 절차

To 0.023 g (0.10 mmol) (S)—N-{1-[4-(3-hydroxy-azetidin-1-yl)-phenyl]-ethyl}-acetamide (V.1) in 5 mL THF are added 0.017 mL (0.12 mmol) TEA and the mixture is cooled to 0° C. 0.008 mL (0.10 mmol) methanesulfonyl chloride are added dropwise and the mixture is stirred for 2 h at 0° C. Water is added and the aq. phase is extracted with ethyl acetate (2×). The combined organic layers are dried (MgSO4) and concentrated. The residue is taken up in 1.0 mL DMA and is added to a mixture of 0.014 g (0.12 mmol) 2,3-difluoro-4-methylphenol and 0.039 g (0.12 mmol) Cs2CO3 in 1.0 mL DMA. The resulting mixture is stirred for 12 h at 100° C. After cooling the mixture is directly purified by HPLC (MeOH/water (+0.1% NH4OH)) to yield the desired product.

후처리

  1. extractionthe aq. phase is extracted with ethyl acetate (2×)
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. concentrationconcentrated
  4. stirringThe resulting mixture is stirred for 12 h at 100° C
  5. temperatureAfter cooling the mixture
  6. customis directly purified by HPLC (MeOH/water (+0.1% NH4OH))

출처 및 근거

ORD 기록
ord-61c7ced06ea8445ebbf1b886e10cbb3f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530461B2

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