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 2173008노트

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HRID 2173008 반응식
[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]

참가 물질

7

반응물 4

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

생성물 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-dicarboxylate수율 92%

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff4b0ec4f3ba488b984951459685e1a4
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056844B2

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