Potassium Carbonate → 5-Difluoromethoxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 225556

반응식

HRID 225556 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:25]([F:32])([F:31])C(OCC)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17][CH:25]([F:32])[F:31])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 18630963tert-Butyl 5-hydroxy-1,3-dihydro-2H-isoindole-2-carboxylate

생성물 1

HCID 577532125-Difluoromethoxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

A mixture containing 0.68 mmol 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (CAS: 226070-47-9), 0.68 mmol potassium carbonate and 0.68 mmol ethyl chlorodifluoroacetate in 1.5 ml DMF was stirred overnight at 65° C. The mixture was then partitioned between ethyl acetate and water and the organic phase was then separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: n-heptane/ethylacetate) to afford the title compound as a white solid (40% yield).

후처리

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organic phase was then separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (eluant: n-heptane/ethylacetate)

출처 및 근거

ORD 기록
ord-7eeace9b5415458084a6e8d730a81053
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557114B2

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