Hydrochloric Acid → HCID 59497353、化合物

HRID 1747473ノート

反応式

HRID 1747473 の反応式
C(OC([N:8]1[C:16]2[C:11](=[C:12]([CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[C:20]3=[O:34])[CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.[OH-].[Li+].Cl>O1CCOCC1.O.C(OCC)(=O)C>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][NH:8]2)=[C:12]([CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:20]2=[O:34])[CH:13]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59497231HCID 59497231、化合物

生成物 1

HCID 59497353HCID 59497353、化合物収率 76%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

6-Chloro-4-[3-(2-methoxycarbonyl-ethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl]-indole-1-carboxylic acid tert-butyl ester 270 mg (0.56 mmol) is taken up in dioxane 4 mL and then the lithium hydroxide 53 mg 2.23 mmol in water is added to the solution. The reaction is stirred for 2 hours and then made acidic by the addition of 1N HCl. The compound is then extracted into ethyl acetate and then the ethyl acetate is dried (MgSO4) filtered and evaporated in vacuo. The oil is taken up in dichloromethane and TFA is added. The reaction is stirred for 1 hour and then evaporated in vacuo to give a solid that is taken up in ethyl acetate and precipitated with hexanes. The solid is collected and washed with hexanes to give the title compound (156 mg, 0.42 mmol, 76%). LCMS (ESMS): m/z 370.8 (M+H+).

後処理

  1. extractionThe compound is then extracted into ethyl acetate
  2. dry with materialthe ethyl acetate is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. additionTFA is added
  6. stirringThe reaction is stirred for 1 hour
  7. customevaporated in vacuo
  8. customto give a solid
  9. customprecipitated with hexanes
  10. customThe solid is collected
  11. washwashed with hexanes

出典と根拠

ORDレコード
ord-40a3a842fbcf4d8cbebe43e57ac49899
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

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