Water → HCID 22103733, compound

HRID 1457208Notes

Reaction equation

HRID 1457208 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[CH:29]([OH:41])[C:30]3[O:31][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:33][N:34]=3)=[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[CH:29]([OH:41])[C:30]3[O:31][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:33][N:34]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])[O:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22103475N-(3,4-Dimethyl-5-isoxazolyl)-2′-[hydroxy(5-phenyl-2-oxazolyl)methyl]-N-[(2-methoxyethoxy)methyl]-4′-(2-oxazolyl)[1,1′-biphenyl]-2-sulfonamide

Product 1

HCID 22103733HCID 22103733, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Step (B) (200 mg, 0.305 mmol) in 10.2 ml of CH3CN, Me3SiCl (199 mg, 1.83 mmol) was added and followed by NaI (274 mg, 1.83 mmol). The mixture was stirred at room temperature for 1 hr. Additional Me3SiCl (199 mg, 1.83 mmol) and NaI (274 mg, 1.83 mmol) were added in three portions and the reaction was stirred for additional 5.5 hr. The mixture was added to 5 ml H2O and 50 ml EtOAc. The organic layer was washed with sat. Na2S2 O3, brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 27% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 73% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (65 mg, 37%) as a white solid, m.p. 125°-135° C. (amorphous).

Workup

  1. stirringthe reaction was stirred for additional 5.5 hr
  2. washThe organic layer was washed with sat. Na2S2 O3, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC on an ODS S10 column

Sources & evidence

ORD record
ord-09765838cc434195b83161283124a2c8
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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