Sodium borohydride → Methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-hydroxymethylfuran-3-yl)-2-(4-methylbenzene-sulfonyloxy)-benzoate

HRID 1778346ノート

反応式

HRID 1778346 の反応式
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:11]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:14]([C:32]2[CH:36]=[CH:35][O:34][C:33]=2[CH:37]=[O:38])=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:42]([O:41][C:39]([N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[C:11]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:14]([C:32]2[CH:36]=[CH:35][O:34][C:33]=2[CH2:37][OH:38])=[CH:13][CH:12]=1)=[O:40])([CH3:44])([CH3:45])[CH3:43]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 86684729Methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-formylfuran-3-yl)-2-(4-methylbenzenesulfonyloxy)-benzoate2 回

生成物 1

HCID 86684728Methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-hydroxymethylfuran-3-yl)-2-(4-methylbenzene-sulfonyloxy)-benzoate収率 97.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium borohydride (0.304 g) was added to a solution of methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-formylfuran-3-yl)-2-(4-methylbenzenesulfonyloxy)-benzoate (Intermediate 22, 3.9 g) in ethanol (50 mL) and the mixture was stirred for 15 minutes. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-hydroxymethylfuran-3-yl)-2-(4-methylbenzene-sulfonyloxy)-benzoate (3.82 g) as a white solid.

後処理

  1. customThe mixture was evaporated to dryness
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-71574d8d05eb434a909ee6eb6a750c46
出典データセット
uspto-grants-2016_02
特許番号
US09266896B2

反応ノート

読み込み中…