Hydrochloric Acid → HCID 22648854, 화합물

HRID 393284노트

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HRID 393284 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=1)=O.CC[N:15]([CH2:18]C)CC.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C([NH2:43])=O>CN(C=O)C.CCOC(C)=O>[CH3:12][C:7]1[CH:6]=[C:5]([C:3]2[N:43]=[CH:18][N:15]([C:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:2]=2)[CH:10]=[CH:9][C:8]=1[OH:11]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 112184492-Bromo-1-(4-hydroxy-3-methylphenyl)ethanone

생성물 1

HCID 22648854HCID 22648854, 화합물수율 71%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

A solution of 2-bromo-1-(4-hydroxy-3-methylphenyl)ethanone (400 mg, 1.75 mmol) in formamide (10 mL) was stirred at 190° C. for 5 h. The excess formamide was distilled under reduced pressure. The residue was taken in EtOAc (50 mL) and the resulting solution was successively washed with pH 7.0 buffer solution (10 mL), water (10 mL) and brine (10 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. A solution of the residue, Et3N (0.88 g, 8.73 mmol) and triphenylmethyl chloride (584 mg, 2.10 mmol) in DMF (10 mL) was stirred at 60° C. for 3 h. The reaction mixture was cooled to 25° C., acidified with aqueous 1.0 N HCl solution and diluted with EtOAc (200 mL). The resulting mixture was successively washed with water (3×50 mL) and brine (50 mL), then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 1:1) to yield the title compound (514 mg, 71% yield).

후처리

  1. distillationThe excess formamide was distilled under reduced pressure
  2. washthe resulting solution was successively washed with pH 7.0 buffer solution (10 mL), water (10 mL) and brine (10 mL)
  3. dry with materialthen was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting mixture was successively washed with water (3×50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (Hexane:EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-ffd4d76f870e4305ac6cc04a520d9816
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806265B2

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