Lithium Chloride → (4-amino-3-vinylbenzyl)carbamic Acid t-butyl Ester

HRID 2358370ノート

反応式

HRID 2358370 の反応式
[Cl-].[Li+].[C:3]([O:7][C:8](=[O:19])[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13](I)[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC>CN(C=O)C>[C:3]([O:7][C:8](=[O:19])[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([CH:20]=[CH2:21])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4]

参加物

5

反応物 3

HCID 433294Lithium ChlorideHCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamateHCID 53438229Tri(butyl)vinyltin

生成物 1

HCID 68457485(4-amino-3-vinylbenzyl)carbamic Acid t-butyl Ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A 50 ml two-neck round bottom flask was filled with argon gas and the solution of tetrakis(triphenyl phosphine)palladium(0) (123.7 mg, 0.107 mmol, 0.06 eq.) and lithium chloride (211.9 mg, 4.998 mmol, 2.8 eq.) in DMF was put into the flask. To the solution was added (4-amino-3-iodobenzyl) carbamic acid t-butyl ester (621.4 mg, 1.875 mmol, 1 eq.) and tributylvinyltin (782.5 mg, 2.678 mmol, 1.5 eq.). The mixture solution was heated to 90° C. to reflux for one night. After confirming the completion of the reaction with TLC, the reaction solution was extracted with methylenechloride, washed with water and brine, dried over Na2SO4, filtered and evaporated. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=3/1) to yield brown liquid.

後処理

  1. additionA 50 ml two-neck round bottom flask was filled with argon gas
  2. temperatureto reflux for one night
  3. customthe completion of the reaction with TLC
  4. extractionthe reaction solution was extracted with methylenechloride
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=3/1)
  10. customto yield brown liquid

出典と根拠

ORDレコード
ord-7de3eef4449f49b7a80b05a4e32b4a68
出典データセット
uspto-grants-2010_07
特許番号
US07763657B2

反応ノート

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