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

HRID 2358370노트

반응식

HRID 2358370 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7de3eef4449f49b7a80b05a4e32b4a68
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763657B2

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