Oxalyl chloride → Methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate

HRID 1778393노트

반응식

HRID 1778393 반응식
[C:1]([C:5]([NH:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][C:21]([OH:23])=O)[C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:6])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[C:1]([C:5]([NH:7][C:8]1[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:14]2[C:15]([C:21](=[O:23])[CH2:20][CH2:19][O:18]2)=[CH:16][CH:17]=1)=[O:6])([CH3:3])([CH3:4])[CH3:2]

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 66686291Methyl 2-tert-butylcarbonylamino-6-(2-carboxyethoxy)-benzoate2회

생성물 1

HCID 66693192Methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate수율 45%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 2-tert-butylcarbonylamino-6-(2-carboxyethoxy)-benzoate (Intermediate 78, 2.73 g) in DCM (50 mL) was stirred at room temperature. DMF (5 drops) was added, followed by oxalyl chloride (2.0 g). After 30 minutes of stirring, the mixture was concentrated in vacuo and the residue was redissolved in DCM and evaporated to dryness. The residue was dissolved in DCM (50 mL) and aluminium chloride (3.38 g) was added. The resultant mixture was stirred at room temperature for 5 hours then diluted with more DCM and washed with ice/water. After separation, the aqueous phase was extracted with more DCM and the combined organic layers were washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 10-40% to give methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate (1.16 g) as a white crystalline solid.

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue was redissolved in DCM
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in DCM (50 mL)
  5. additionaluminium chloride (3.38 g) was added
  6. stirringThe resultant mixture was stirred at room temperature for 5 hours
  7. additionthen diluted with more DCM
  8. washwashed with ice/water
  9. customAfter separation
  10. extractionthe aqueous phase was extracted with more DCM
  11. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated in vacuo
  15. customthe residue was purified by chromatography on silica
  16. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 10-40%

출처 및 근거

ORD 기록
ord-9375441d21384443ad04d701d3985763
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266896B2

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