Diethyl Ether → HCID 58360463, 화합물

HRID 632552

반응식

HRID 632552 반응식
[H-].[Na+].[Cl-].[CH3:4][S+](C)(C)=O.[CH3:9][O:10][C:11]([C:13]1[S:14][C:15]([C:35]#[C:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:16][C:17]=1[N:18]([C:26]([CH:28]1[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]1)=[O:27])[CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)=[O:12].C(OCC)C>CS(C)=O.C1COCC1.[Cl-].[Na+].O>[CH3:9][O:10][C:11]([C:13]1[S:14][C:15]([C:35]#[C:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:16][C:17]=1[N:18]([C:26]([CH:28]1[CH2:29][CH2:30][CH:31]([CH3:34])[CH2:32][CH2:33]1)=[O:27])[CH:19]1[CH2:20][CH2:21][C:22]2([O:25][CH2:4]2)[CH2:23][CH2:24]1)=[O:12]

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 58114000HCID 58114000, 화합물

생성물 1

HCID 58360463HCID 58360463, 화합물수율 37%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

NaH (140 mg of a 60% oil dispersion, 3.50 mmol) was added in portions to a solution of trimethylsulfoxonium chloride (452 mg, 3.51 mmol) in DMSO (8.0 mL) at room temperature. After 15 min, a solution of 5-(3,3-dimethyl-but-1-ynyl)-3-[(4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (1.34 g, 2.93 mmol) in THF (8.0 mL) was added dropwise. After 3 h, brine was added and the reaction extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give a viscous yellow oil. Trituration with ethyl ether and hexanes provided 5-(3,3-dimethyl-but-1-ynyl)-3-[(4-methyl-cyclohexanecarbonyl)-(1-oxa-spiro[2.5]oct-6-yl)-amino]-thiophene-2-carboxylic acid methyl ester (509 mg, 37%) as a colorless solid.

후처리

  1. waitAfter 3 h
  2. extractionthe reaction extracted with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a viscous yellow oil

출처 및 근거

ORD 기록
ord-136b43c6c0984e44ac86f81e455a481a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321753B2

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