Sodium Thiosulfate → HCID 17747370, compound

HRID 1715357Notes

Reaction equation

HRID 1715357 reaction equation
[F:1][C:2]([F:21])([F:20])[CH:3]([C:5]1[S:9][C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[N:7][CH:6]=1)[OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[F:21][C:2]([F:1])([F:20])[C:3]([C:5]1[S:9][C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[N:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 68510739HCID 68510739, compound

Product 1

HCID 17747370HCID 17747370, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the crude product I2 in DCM was treated with Dess-Martin Periodinane (3.0 eq.) and stirred for 3 h at RT. Aq. sodium thiosulfate was added and the aqueous phase was extracted with DCM. The combined organic phase was dried (Na2SO4) and solvents were removed under reduced pressure. The crude was purified by RP-HPLC (Waters SYMMETRY C18, 7 micron, 19×300 mm; flow: 20 mL/min; Gradient: A: H2O (+0.1% TFA); B: MeCN (+0.1% TFA); 60% A linear to 10% A in 14 min) to afford the title compound as a solid after freeze drying the desired fractions. 1H NMR (300 MHz, DMSO-d6, 300K) δ 7.69-7.50 (3H, m), 8.27-7.92 (4H, m), 8.55 (1H, s). MS (ES+) C15H8F3NOS requires: 307, found: 308 (M+H)+ and 326 (M+H+H20)+.

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. dry with materialThe combined organic phase was dried (Na2SO4) and solvents
  3. customwere removed under reduced pressure
  4. customThe crude was purified by RP-HPLC (Waters SYMMETRY C18, 7 micron, 19×300 mm

Sources & evidence

ORD record
ord-826b0702c98a4293a955429c623b2235
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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