Water → 4-(6-Bromo-pyridin-2-yl)-4-methyl-2,2-dioxo-2lambda*6*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester

HRID 474053Notes

Reaction equation

HRID 474053 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[N:15]=2)([CH3:13])[CH2:11][O:10][S:9]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[OH2:25]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[N:15]=2)([CH3:13])[CH2:11][O:10][S:9]1(=[O:25])=[O:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962Water2×HCID 6344DichloromethaneHCID 1317311634-(6-Bromo-pyridin-2-yl)-4-methyl-2-oxo-2lambda*4*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 1317311644-(6-Bromo-pyridin-2-yl)-4-methyl-2,2-dioxo-2lambda*6*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(6-bromo-pyridin-2-yl)-4-methyl-2-oxo-2lambda*4*-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (8.83 g, 23.4 mmol) in acetonitrile (60 ml) and H2O (30.0 ml) was added RuCl3 hydrate (0.971 g, 4.68 mmol) and NaIO4 (10.01 g, 46.8 mmol). The reaction mixture was stirred at 0° C. for 2 h. H2O and DCM were added, the phases were separated and the aq. phase was twice reextracted with DCM. The combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DCM and filtered through silica gel, the filtrate was evaporated and the residue was triturated with TBME (10 ml) and n-hexane (100 ml). The resulting precipitate was filtered and washed with n-hexane to yield the title compound as a colourless crystalline solid. HPLC RtH4=1.16 min; ESIMS: 393, 395 [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 7.63-7.59 (m, 1H), 7.47-7.42 (m, 2H), 4.73 (d, 1H), 4.47 (d, 1H), 2.00 (s, 3H), 1.52 (s, 9H).

Workup

  1. customthe phases were separated
  2. washphases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM
  7. filtrationfiltered through silica gel
  8. customthe filtrate was evaporated
  9. customthe residue was triturated with TBME (10 ml) and n-hexane (100 ml)
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with n-hexane

Sources & evidence

ORD record
ord-112ff96b42444d37983e43fa862d66b9
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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