Potassium Carbonate → 3-(2-tert-Butyoxycarbonylaminoethylamino)-4-nitrobenzoic acid methyl ester

HRID 18483

반응식

HRID 18483 반응식
O1CCOC[CH2:2]1.C([O-])([O-])=O.[K+].[K+].F[C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[C:17]([OH:19])=[O:18].[C:26]([NH:33][CH2:34][CH2:35][NH2:36])([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CN(C=O)C>[CH3:2][O:19][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:14]([NH:36][CH2:35][CH2:34][NH:33][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH:15]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 187201N-BOC-ethylenediamineHCID 2306533-Fluoro-4-nitrobenzoic acid

생성물 1

HCID 593455393-(2-tert-Butyoxycarbonylaminoethylamino)-4-nitrobenzoic acid methyl ester수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A 2 L flask equipped with a stir bar was charged with 1,4-dioxane (300 mL), DMF (40 mL), K2CO3 (10 g) and 3-fluoro-4-nitrobenzoic acid (9.7 g). Mono-N-Boc-1,2-diaminoethane (8.6 g) was added to the reaction mixture and stirred for 12 h at 60° C. The reaction mixture was concentrated and the residue was dissolved in CH2Cl2 (400 mL) and H2O (500 mL). The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with CH2Cl2 (2×100 mL). The organic phases were combined and washed with H2O (5×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound as an orange solid (14 g, 84%).

후처리

  1. customA 2 L flask equipped with a stir bar
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in CH2Cl2 (400 mL)
  4. customThe heterogeneous mixture was transferred to a separatory funnel
  5. customwhere the aqueous phase was separated
  6. extractionre-extracted with CH2Cl2 (2×100 mL)
  7. washwashed with H2O (5×100 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-17ab5f1b455b4bb2b7d4a3a329553865
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741355B2

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