Hydrochloric Acid → 5-[1-Fluoro-3-hydroxy-7-(4-formyl-4-methyl-pentyl)-naphthalen-2-yl]-1,1-dioxo-[1,2,5]thiadiazolidin-3-one

HRID 889284노트

반응식

HRID 889284 반응식
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH:10]=2)[CH:5]=[C:4]([OH:20])[C:3]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1.C(N(CC)CC)C.O.Cl>CS(C)=O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([CH:16]=[O:17])([CH3:19])[CH3:18])[CH:10]=2)[CH:5]=[C:4]([OH:20])[C:3]=1[N:21]1[S:25](=[O:26])(=[O:27])[NH:24][C:23](=[O:28])[CH2:22]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 177472965-[1-Fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

생성물 1

HCID 177475235-[1-Fluoro-3-hydroxy-7-(4-formyl-4-methyl-pentyl)-naphthalen-2-yl]-1,1-dioxo-[1,2,5]thiadiazolidin-3-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a stirred solution of 5-[1-fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.00 g, 2.23 mmol) in anhydrous DMSO (10 ml) at room temperature was added triethylamine (2.17 mL, 15.6 mmol) followed by a slow addition of a solution of sulfur trioxide pyridine complex (1.28 g, 8.02 mmol) in anhydrous DMSO (12 mL). The reaction mixture was stirred for 30 min and cold water (70 mL) was slowly added. The above content was acidified with 3 N HCl to pH 2.5, extracted twice with EtOAc, washed with brine, dried over MgSO4, and concentrated to yield the title compound as a light brown solid. Retention time=1.22 min (Method A); MS (M−H)−=407.

후처리

  1. extractionextracted twice with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-23016b81fa0b43678f342aa48249d70f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252820B2

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