Hydrochloric Acid → HCID 178485999、化合物

HRID 2118231ノート

反応式

HRID 2118231 の反応式
[CH2:1]([O:8][C:9](=[O:19])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:24][C:25](=[O:28])[CH2:26]Br)(C)(C)C.[OH-].[Na+].Cl>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C:9]([N:10]([CH3:11])[C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][CH2:26][C:25]([OH:28])=[O:24])[CH2:14][CH2:13]1)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate2 回HCID 178485998HCID 178485998、化合物

生成物 1

HCID 178485999HCID 178485999、化合物収率 99.4%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒2 回HCID 1140Toluene溶媒

実験手順

To a suspension of 15.0 g (57 mmol) of trans-(4-hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester in 230 mL of toluene were added 16.8 mL (114 mmol, 2 eq) of bromo-acetic acid tert-butyl ester and 1.93 g (5.7 mmol, 0.1 eq) of tetra-n-butylammonium hydrogensulfate and 400 mL of 50% aqueous NaOH. The mixture was stirred at RT for 4 h, additional 1.93 g (5.7 mmol, 0.1 eq) of tetra-n-butyl-ammoniumhydrogensulfate and 4.2 mL of bromo-acetic acid tert-butyl ester were added, and stirring was continued over night. The solution was concentated and acidified by adding 400 mL of 37% HCl. The solution was extracted with EtOAc, the organic phase was washed with brine and dried over Na2SO4. The solvent was removed to yield 18.2 g (quantitative) trans-[4-(benzyloxycarbonyl-methyl-amino)-cyclohexyloxy]-acetic acid as white solid, MS: 320 (M−H)−.

後処理

  1. stirringstirring
  2. waitwas continued over night
  3. extractionThe solution was extracted with EtOAc
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed

出典と根拠

ORDレコード
ord-a1fe029bb9e44818b2bf519e300b46a7
出典データセット
uspto-grants-2008_10
特許番号
US07442791B2

反応ノート

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