Sodium Carbonate → HCID 89923757, 화합물

HRID 1752648노트

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HRID 1752648 반응식
[OH:1][C@@H:2]([C:7]1[C:8]([I:18])=[C:9]2[CH:16]=[CH:15][N:14]([CH3:17])[C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4].C(O[C:23]([CH3:26])([CH3:25])[CH3:24])(=O)C.C([O-])([O-])=O.[Na+].[Na+]>>[C:23]([O:1][C@@H:2]([C:7]1[C:8]([I:18])=[C:9]2[CH:16]=[CH:15][N:14]([CH3:17])[C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4])([CH3:26])([CH3:25])[CH3:24]

참가 물질

4

반응물 3

HCID 10340Sodium CarbonateHCID 10908tert-Butyl acetateHCID 89933754HCID 89933754, 화합물

생성물 1

HCID 89923757HCID 89923757, 화합물수율 72%

실험 절차

A solution of (S)-methyl 2-hydroxy-2-(4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (9.6 g, 26.7 mmol) in tert-butyl acetate (349 ml, 2583 mmol) was treated dropwise with HClO4 (12.37 ml, 144 mmol). After 1 h, the reaction mixture was poured into 2M Na2CO3 and the layers partitioned. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by ISCO (0-60% EtOAc-hexanes) to afford the title compound as a white foam (8.0 g, 71%). 1H NMR (CHLOROFORM-d) δ 7.13 (d, J=3.3 Hz, 1H), 6.30 (d, J=3.3 Hz, 1H), 5.75 (s, 1H), 3.84 (s, 3H), 3.67 (s, 3H), 2.73 (s, 3H), 1.25 (s, 9H). LC/MS (m/z) ES+=416.9 (M+1)+

후처리

  1. customthe layers partitioned
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by ISCO (0-60% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-eda028cd2a714ae59759903e37ed8833
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163023B2

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