Sodium Iodide → HCID 10907333, compound

HRID 1457190Notes

Reaction equation

HRID 1457190 reaction equation
[CH3:1][C:2]([NH:5][C:6](=[O:42])[CH2:7][C:8]1[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:25]([N:28]([C:35]2[O:39][N:38]=[C:37]([CH3:40])[C:36]=2[CH3:41])COCCOC)(=[O:27])=[O:26])=[CH:10][CH:11]=[C:12]([C:14]2[O:15][CH:16]=[CH:17][N:18]=2)[CH:13]=1)([CH3:4])[CH3:3].[Si](Cl)(C)(C)C.[Na+].[I-].CCOC(C)=O>CC#N>[CH3:4][C:2]([NH:5][C:6](=[O:42])[CH2:7][C:8]1[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[S:25]([NH:28][C:35]2[O:39][N:38]=[C:37]([CH3:40])[C:36]=2[CH3:41])(=[O:27])=[O:26])=[CH:10][CH:11]=[C:12]([C:14]2[O:15][CH:16]=[CH:17][N:18]=2)[CH:13]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 8857Ethyl AcetateHCID 22103556HCID 22103556, compound

Product 1

HCID 10907333HCID 10907333, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the title compound of Step (D) (45 mg, 0.075 mmol) in 3 ml of CH3CN, Me3SiCl (41 mg, 0.38 mmol) was added and followed by NaI (57 mg, 0.38 mmol). The mixture was stirred at room temperature for 1.5 hrs. Additional Me3SiCl (32 mg, 0.3 mmol) and NaI (46 mg, 0.3 mmol) were added in twice after stirred for 30 min and 1 hr. 3 ml H2 O and 30 ml EtOAc were added. The organic layer was washed with sat. Na2S2O3, brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 33% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 67% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (23 mg, 60%) as a white solid, m.p. 117°-123° C. (amorphous).

Workup

  1. stirringafter stirred for 30 min and 1 hr
  2. washThe organic layer was washed with sat. Na2S2O3, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC on an ODS S10 column

Sources & evidence

ORD record
ord-384a150aa69c4b71a0ab34a69e5664b3
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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