Diisopropylethylamine → HCID 58235000, 화합물

HRID 1947363노트

반응식

HRID 1947363 반응식
Cl.[CH3:2][C@H:3]1[O:8][CH2:7][CH2:6][NH:5][CH2:4]1.C(N(C(C)C)C(C)C)C.[Br:18][C:19]1[CH:20]=[C:21]([C:35]([O:37][CH3:38])=[O:36])[CH:22]=[C:23]2[C:28]=1[O:27][C:26](S(CC)(=O)=O)=[CH:25][C:24]2=[O:34]>C(Cl)Cl>[Br:18][C:19]1[CH:20]=[C:21]([C:35]([O:37][CH3:38])=[O:36])[CH:22]=[C:23]2[C:28]=1[O:27][C:26]([N:5]1[CH2:6][CH2:7][O:8][C@H:3]([CH3:2])[CH2:4]1)=[CH:25][C:24]2=[O:34]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 42609645(2R)-2-Methylmorpholine hydrochlorideHCID 58235035methyl 8-bromo-2-(ethylsulfonyl)-4-oxo-4H-chromene-6-carboxylate

생성물 1

HCID 58235000HCID 58235000, 화합물수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of (R)-2-methylmorpholine hydrochloride (0.436 g, 3.17 mmol) and N-ethyl-N-isopropylpropan-2-amine (1.184 mL, 6.80 mmol) in DCM (5 mL) was added dropwise to a stirred solution of methyl 8-bromo-2-(ethylsulfonyl)-4-oxo-4H-chromene-6-carboxylate (0.85 g, 2.27 mmol) in DCM (10 mL) at 10° C. under argon. The resulting solution was stirred at RT for 3 hrs. The reaction mixture was quenched with 1M HCl, the phases were separated, the organic phase was washed with brine dried over magnesium sulfate and concentrated to afford the crude product which was purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM. The solvent was evaporated to dryness to afford after a trituration with ether, methyl 8-bromo-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (0.760 g, 88%) as a pale yellow foam. Mass Spectrum: M+H+ 382. The reaction was repeated on a similar scale before proceeding to the next step.

후처리

  1. customThe reaction mixture was quenched with 1M HCl
  2. customthe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas purified by flash chromatography on silica gel eluting with 0 to 10% MeOH in DCM
  8. customThe solvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-4406f003126d40d1abbfb7d10c7c2bd1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399460B2

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