Water → HCID 22103720, compound

HRID 1457218Notes

Reaction equation

HRID 1457218 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[O:19][CH:20]=[CH:21][N:22]=2)[CH:15]=[CH:14][C:13]=1[C:23]1[C:24]([S:29]([N:32]([C:39]2[O:43][N:42]=[C:41]([CH3:44])[C:40]=2[CH3:45])COCCOC)(=[O:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=1.[Si](Cl)(C)(C)C.[Na+].[I-].O>CC#N.CCOC(C)=O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH2:11][C:12]1[CH:17]=[C:16]([C:18]2[O:19][CH:20]=[CH:21][N:22]=2)[CH:15]=[CH:14][C:13]=1[C:23]1[C:24]([S:29]([NH:32][C:39]2[O:43][N:42]=[C:41]([CH3:44])[C:40]=2[CH3:45])(=[O:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22103827HCID 22103827, compound

Product 1

HCID 22103720HCID 22103720, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Step (A) in 4 ml of CH3CN, Me3SiCl (174 mg, 1.6 mmol) was added and followed by NaI (240 mg, 1.6 mmol). The mixture was stirred at room temperature for 20 min. Additional Me3SiCl (74 mg, 1.6 mmol) and NaI (240 mg, 1.6 mmol) were added in four portions and the reaction was stirred for additional 1 hr and 10 min. The reaction mixture was then added to 3 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 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 (43 mg, 40% for two steps) as a white solid, m.p. 135°-142° C. (amorphous).

Workup

  1. stirringthe reaction was stirred for additional 1 hr and 10 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-79eef658045a488eb265461e2855c92e
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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