Dimethylformamide → Methyl 3-cyano-4-isopropoxybenzoate

HRID 1714584노트

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HRID 1714584 반응식
N([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)[C@@H](C(O)=O)C.C([O-])([O-])=[O:18].[K+].[K+].C(C(N)CBr)([O:25][C:26](C)([CH3:28])[CH3:27])=O.[CH3:34][N:35](C=O)C>O>[C:34]([C:15]1[CH:16]=[C:11]([CH:12]=[CH:13][C:14]=1[O:25][CH:26]([CH3:28])[CH3:27])[C:10]([O:9][CH3:7])=[O:18])#[N:35]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70832N-Cbz-d-alanineHCID 22273677Boc-aminoethyl bromide

생성물 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoate수율 55%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

To a solution of compound 3 (5.000 g, 17 mmol) in DMF (15 mL) was added K2CO3 (3.51 g, 26 mmol) and Boc-2-amino ethyl bromide (4.56 g, 20.35 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and concentrated. Purification with column chromatography (Hexanes/EtOAc 50:50) gave the product 4 (4.08 g, 55%) as white solid.

후처리

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification with column chromatography (Hexanes/EtOAc 50:50)

출처 및 근거

ORD 기록
ord-1a1773d76b4a41e094abfac387b776c4
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795448B2

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