Tetrahydrofuran → HCID 59464121, compound

HRID 1713895Notes

Reaction equation

HRID 1713895 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+].[C:30]([O:33][CH2:34][CH3:35])(=[O:32])[CH3:31].[CH2:36]1COCC1>>[CH2:20]([O:19][C:18]([NH:17][C:5]1[CH:6]=[CH:7][C:8]([CH:10]2[CH2:15][CH2:14][C:13](=[C:31]([CH3:36])[C:30]([O:33][CH2:34][CH3:35])=[O:32])[CH2:12][CH2:11]2)=[CH:9][C:4]=1[Cl:3])=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran3×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59464124HCID 59464124, compound

Product 1

HCID 59464121HCID 59464121, compoundYield 69%

Procedure

A solution of triethylphosphonopropionate (1.54 g, 6.46 mmol) in THF (10 mL) was added dropwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.28 g, 7.05 mmol) in THF (30 mL) at 10° C. under an argon atmosphere and the mixture was warmed to room temperature. The reaction mixture was cooled to 10° C. and then a solution of benzyl [2-chloro-4-(4-oxocyclohexyl)phenyl]carbamate (2.36 g, 5.87 mmol) in THF (10 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 4 h. A saturated aqueous solution of ammonium chloride (50 mL) and ethyl acetate (70 mL) were added. The layers were separated and the organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to leave an oil. Purification by column chromatography, using a gradient of 11-66% ethyl acetate:isohexane as eluent, gave the title compound (1.80 g, 69%) as a solid; 1H NMR δ 1.34 (3H, t), 1.46-1.53 (2H, m), 1.93 (3H, s), 1.95-2.1 (4H, m), 2.67-2.87 (2H, m), 3.13-3.24 (1H, m), 4.22 (2H, q), 5.24 (2H, s), 7.1-7.18 (2H, m), 7.21 (1H, d), 7.33-7.5 (5H, m), 8.08 (1H, d); MS m/e (M−H)− 440.

Workup

  1. temperatureThe reaction mixture was cooled to 10° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customThe layers were separated
  4. washthe organic layer was washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto leave an oil
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-ddea678bf9f74aeaa748ac7ea906f6e6
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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