Sodium Carbonate → HCID 89923757, compound

HRID 1752648Notes

Reaction equation

HRID 1752648 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 89923757HCID 89923757, compoundYield 72%

Procedure

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)+

Workup

  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)

Sources & evidence

ORD record
ord-eda028cd2a714ae59759903e37ed8833
Source dataset
uspto-grants-2015_10
Patent number
US09163023B2

Reaction notes

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