Dichloromethane → HCID 59696193, compound

HRID 900334Notes

Reaction equation

HRID 900334 reaction equation
[Si](I)(C)(C)C.[CH3:6][O:7][C:8](=[O:46])[CH:9]([NH:38]C(OC(C)(C)C)=O)[CH2:10][S:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:30]4[O:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[C:29]=4[CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(Cl)Cl.C(=O)(O)[O-].[Na+]>O>[CH3:6][O:7][C:8](=[O:46])[CH:9]([NH2:38])[CH2:10][S:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[C:30]4[O:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[C:29]=4[CH:28]=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 57588590HCID 57588590, compound

Product 1

HCID 59696193HCID 59696193, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TMS-I (290 mg, 0.21 mL, 1.45 mmol) was added dropwise to a stirred solution of methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethyl-sulfanyl)-propionate (748 mg, 1.32 mmol) in anhyd methylene chloride (20 mL). The reaction mixture was stirred at room temperature for 20-30 min (TLC control), and then diluted with water (20 mL). Sat'd aq sodium bicarbonate solution was added to adjust the solution to pH 8-9. The reaction mixture was extracted with diethyl ether (2×30 mL). The combined organic extracts were washed with water, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (5% methanol in methylene chloride) afforded the title compound has a pale yellow solid (596 mg).

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether (2×30 mL)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-61811932520a4fc99023233d978e8078
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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