Bromomethyl pivalate → Pivaloyloxymethyl (5R,6R)-2-ethylsulfinyl-6-(-2-hydroxy-2-propyl)-pen-2-em-3-carboxylate

HRID 1253160노트

반응식

HRID 1253160 반응식
[C:1]([O:7][CH2:8]Br)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:10]([S:12]([C:14]1[S:15][C@@H:16]2[C@H:23]([C:24]([OH:27])([CH3:26])[CH3:25])[C:22](=[O:28])[N:17]2[C:18]=1[C:19]([O-:21])=[O:20])=[O:13])[CH3:11].[Li+]>CN(C=O)C.CCOC(C)=O>[CH2:10]([S:12]([C:14]1[S:15][C@@H:16]2[C@H:23]([C:24]([OH:27])([CH3:25])[CH3:26])[C:22](=[O:28])[N:17]2[C:18]=1[C:19]([O:21][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:20])=[O:13])[CH3:11]

참가 물질

5

반응물 2

HCID 15916453Bromomethyl pivalateHCID 131715542lithium (5R,6R)-2-ethylsulfinyl-6-(2-hydroxy-2-propyl)-pen-2-em-3-carboxylate

생성물 1

HCID 54331280Pivaloyloxymethyl (5R,6R)-2-ethylsulfinyl-6-(-2-hydroxy-2-propyl)-pen-2-em-3-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Pivaloyloxymethyl bromide (29.3 mg, 0.15 mmol) is added to a suspension of lithium (5R,6R)-2-ethylsulfinyl-6-(2-hydroxy-2-propyl)-pen-2-em-3-carboxylate (29.5 mg, 0.1 mmol) in anhydrous DMF (0.5 ml). The resulting mixture is stirred under a N2 atmosphere at room temperature for 4 hours. The mixture is diluted with EtOAc, washed repeatedly with water, dried with MgSO4, filtered, and evaporated under vacuum to afford a residue of the title compound. This material is purified by preparative TLC.

후처리

  1. washwashed repeatedly with water
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-d514fbc8af494d208413cb1df38d3292
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04748162

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