Hydroxyamine hydrochloride → (1-[4-(4-Hydroxyimino-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037321노트

반응식

HRID 1037321 반응식
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=S)[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:37][OH:38].C([O-])(=O)C.[Na+]>>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[N:37][OH:38])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86671045{1-[4-(2-Phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

생성물 1

HCID 86671047(1-[4-(4-Hydroxyimino-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester수율 82%

반응 조건

온도
80 °C

실험 절차

A mixture of {1-[4-(2-phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (33.4 mg, 0.069 mmol), hydroxylamine hydrochloride (14.4 mg, 0.207 mmol) and sodium acetate (17 mg, 0.207 mmol) in IMS (5 mL) was stirred at 80° C. for 16 hours. The cooled reaction mixture was partitioned between DCM and water. The aqueous phase was isolated and extracted with DCM. The combined organic extracts were evaporated to dryness. The resultant residue was subjected to flash chromatography (SiO2, 2% MeOH in DCM) to afford the title compound (27.2 mg, 82%) as a pale yellow solid. LCMS (Method A): RT=4.96 min, [M+H]+=483.

후처리

  1. customThe cooled reaction mixture
  2. customwas partitioned between DCM and water
  3. customThe aqueous phase was isolated
  4. extractionextracted with DCM
  5. customThe combined organic extracts were evaporated to dryness

출처 및 근거

ORD 기록
ord-1b0bff899d774719a58e2f62687515fb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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