Water → Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2173008ノート

反応式

HRID 2173008 の反応式
[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:14]([OH:15])[C@H:13]([OH:16])[C@@H:12]2[C@H:10]1[C@H:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[Cl:40])[CH2:35]Br.[OH-].[Na+].O>ClCCl.CCCC[N+](CCCC)(CCCC)CCCC.[Cl-]>[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:14]([O:15][CH2:35][C:34]2[CH:37]=[CH:38][C:39]([Cl:40])=[C:32]([Cl:31])[CH:33]=2)[C@H:13]([OH:16])[C@@H:12]2[C@H:10]1[C@H:11]2[C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 67704267HCID 67704267、化合物

生成物 1

HCID 86695972Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate収率 92%

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3,4-dihydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (450 g, 1.05 mol) in dichloromethane (4.50 L) at room temperature is sequentially added 3,4-dichlorobenzyl bromide (144.73 mL, 238.80 g, 995.32 mmol), tetra-N-butylammonium chloride (58.24 g, 209.54 mmol), and a 50% wt/wt aqueous solution of sodium hydroxide (829.80 mL, 15.72 mol). After 7 hours, dilute the reaction with water (1 L) and separate the phases. Extract the organic phase with brine (500 mL), dry over anhydrous MgSO4, filter and concentrate. Purify the residue by chromatography (2.5 kg of SiO2; eluent: hexane/ethyl acetate 12:1 to 0:1) to give the title compound (539 g, 72% yield).

後処理

  1. customat room temperature
  2. additiondilute
  3. customseparate the phases
  4. extractionExtract the organic phase with brine (500 mL)
  5. dry with materialdry over anhydrous MgSO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue by chromatography (2.5 kg of SiO2; eluent: hexane/ethyl acetate 12:1 to 0:1)

出典と根拠

ORDレコード
ord-ff4b0ec4f3ba488b984951459685e1a4
出典データセット
uspto-grants-2015_06
特許番号
US09056844B2

反応ノート

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