Water → HCID 69848642, compound

HRID 1457216Notes

Reaction equation

HRID 1457216 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8](COCCOC)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:25][CH:26]=[CH:27][N:28]=3)=[CH:20][C:19]=2[CH2:29][CH2:30][N:31]([CH3:41])[C:32](=[O:40])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:11])=[O:10])[O:4][N:3]=1.[Si](Cl)(C)(C)C.[Na+].[I-].O>CC#N.CCOC(C)=O>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:25][CH:26]=[CH:27][N:28]=3)=[CH:20][C:19]=2[CH2:29][CH2:30][N:31]([CH3:41])[C:32](=[O:40])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:10])=[O:11])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22103484HCID 22103484, compound

Product 1

HCID 69848642HCID 69848642, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Step (B) in 1.5 ml of CH3CN, Me3SiCl (34 mg, 0.32 mmol) was added and followed by NaI (48 mg, 0.32 mmol). The mixture was stirred at room temperature for 0.5 hr. Additional Me3SiCl (46 mg, 0.42 mmol) and NaI (63 mg, 0.42 mmol) were added in three portions and the reaction mixture was stirred for additional 1 hr and 45 min. The mixture was then added to 2 ml H2O and 20 ml EtOAc. The organic layer was washed with 1 ml sat. Na2 S2O3, brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 30% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 70% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (7 mg, 23% for two steps) as a white solid, m.p. 98°-106° C. (amorphous).

Workup

  1. stirringthe reaction mixture was stirred for additional 1 hr and 45 min
  2. washThe organic layer was washed with 1 ml sat. Na2 S2O3, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC on an ODS S10 column

Sources & evidence

ORD record
ord-3d0f9909ac234e40abfd5583ca0fa555
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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