Trifluoroacetic acid → Ethyl 2-[4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate

HRID 1901327노트

반응식

HRID 1901327 반응식
C([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH2:26][C:27]3[O:28][C:29]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:30]=4[CH:31]=3)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.F[C:39](F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(OC)C=CC=CC=1>[C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH2:26][C:27]3[O:28][C:29]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:30]=4[CH:31]=3)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)[CH2:9]1)(=[O:5])[CH3:39]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 10323852ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate

생성물 1

HCID 57231814Ethyl 2-[4-[((3S)-1-acetyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate

시약·촉매·용매 1

HCID 7519Anisole용매

실험 절차

2.3 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate was dissolved in 3 ml of anisole. 25 ml of trifluoroacetic acid was added to the above solution with ice cooling, and the resulting mixture was stirred at room temperature for 1 hour. After distilling off trifluoroacetic acid under reduced pressure, the residue thus obtained was adjusted to pH 10-11 with saturated sodium bicarbonate aqueous solution, extracted with chloroform, and then dried. At room temperature, the resulting organic layer was mixed with 2 ml of triethylamine and then with 555 mg of acetyl chloride, followed by stirring at the same temperature for 0.5 hours. After distilling off the solvent, the resulting residue was subjected to silica gel column chromatography using a chloroform/ethanol mixture as an eluant to obtain 1.8 g of the title compound.

후처리

  1. distillationAfter distilling off trifluoroacetic acid under reduced pressure
  2. customthe residue thus obtained
  3. extractionextracted with chloroform
  4. customdried
  5. additionAt room temperature, the resulting organic layer was mixed with 2 ml of triethylamine
  6. stirringby stirring at the same temperature for 0.5 hours
  7. distillationAfter distilling off the solvent

출처 및 근거

ORD 기록
ord-695d0532bfbf47759547d690740b7718
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576343

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