Water → HCID 11082049, compound

HRID 1457221Notes

Reaction equation

HRID 1457221 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8](COCCOC)[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][C:32]([CH3:37])([CH3:36])[C:31]3=[O:38])=[CH:14][CH:15]=[CH:16][CH:17]=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[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][C:32]([CH3:36])([CH3:37])[C:31]3=[O:38])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22103564HCID 22103564, compound

Product 1

HCID 11082049HCID 11082049, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Step (D) (70 mg, 0.11 mmol) in 2.2 ml of CH3CN, Me3SiCl (73 mg, 0.67 mmol) was added and followed by NaI (100 mg, 0.67 mmol). The mixture was stirred at room temperature for 30 min. Additional Me3SiCl (98 mg, 0.90 mmol) and NaI (135 mg, 0.90 mmol) were added in four portions and the reaction was stirred for additional 1 hr and 40 min. The reaction mixture was then added to 2 ml H2O and 30 ml EtOAc. The organic layer was separated and washed with 1 ml saturated aqueous Na2S2O3, brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 29% solvent A (10% MeOH, 90% H2O, 0.1% TFA). and 71% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (37 mg, 62%) as a white solid, m.p. >200° C., dec., Rf=0.5(silica gel, 10:1 CH2Cl2 /MeOH).

Workup

  1. stirringthe reaction was stirred for additional 1 hr and 40 min
  2. customThe organic layer was separated
  3. washwashed with 1 ml saturated aqueous Na2S2O3, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC on an ODS S10 column

Sources & evidence

ORD record
ord-ac7c75580bca4212aae5afa4ec17519d
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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