Dimethylformamide → HCID 91185488, compound

HRID 2417150Notes

Reaction equation

HRID 2417150 reaction equation
P(Cl)(Cl)Cl.[C:5]1([CH2:11][C:12]([NH:14][C@@H:15]2[C:44](=[O:45])[N:17]3[C:18]([C:28]([O:30][CH:31]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[O:29])=[C:19]([C@@H:23]4[CH2:27][CH2:26][CH2:25][O:24]4)[CH2:20][S:21](=O)[C@H:16]23)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C)C=O>ClCCl.C(OCC)(=O)C>[C:5]1([CH2:11][C:12]([NH:14][C@@H:15]2[C:44](=[O:45])[N:17]3[C:18]([C:28]([O:30][CH:31]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[O:29])=[C:19]([C@@H:23]4[CH2:27][CH2:26][CH2:25][O:24]4)[CH2:20][S:21][C@H:16]23)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 131724665HCID 131724665, compound

Product 1

HCID 91185488HCID 91185488, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus trichloride (0.1 ml of a solution containing 0.17 ml/ml in dry dichloromethane) was added to a stirred, ice bath cooled, mixture of the sulphoxide from Example 5 (55 mg) and dry dimethylformamide (0.05 ml) in dry dichloromethane (2 ml). After stirring for 15 minutes at ice bath temperature the mixture was diluted with ethyl acetate (10 ml) and was washed with satd NaHCO3 (2 ml), and brine (3×2 ml). The dried (MgSO4) organic layer was evaporated and the residue was chromatographed on silica gel eluting with ethylacetate/hexane mixtures to give the title compound as an amorphous solid (45 mg), d ppm (CDCl3) 1.42-1.58 (1H, m), 1.79-1.95 (2H, m), 2.21-2.33 (1H, m), 3.24 (1H, d, J 18.7 Hz), 3.56-3.66 (3H, m), 3.71-3.92 (2H, m), 4.84 (1H, dd, J 9.2 and 6.6 Hz), 4.95 (1H, d, J 4.8 Hz), 5.85 (1H, dd, J 9.1 and 4.8 Hz), 6.04 (1H, d, J 9.1 Hz), 6.86 (1H, s), 7.25-7.42 (15H, m).

Workup

  1. additionwas added to a stirred, ice bath
  2. temperaturecooled
  3. washwas washed with satd NaHCO3 (2 ml), and brine (3×2 ml)
  4. dry with materialThe dried (MgSO4) organic layer
  5. customwas evaporated
  6. customthe residue was chromatographed on silica gel eluting with ethylacetate/hexane

Sources & evidence

ORD record
ord-76fc8436aa8a426c943db28873eb185e
Source dataset
uspto-grants-2004_11
Patent number
US06825344B2

Reaction notes

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