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

HRID 1253160ノート

反応式

HRID 1253160 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d514fbc8af494d208413cb1df38d3292
出典データセット
uspto-grants-1988_05
特許番号
US04748162

反応ノート

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