Ethyl acetate hexane → HCID 86649127, compound

HRID 1471046Notes

Reaction equation

HRID 1471046 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.CS(O[C@@H:18]([C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)[CH2:19][CH2:20][C@@H:21](OS(C)(=O)=O)[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)(=O)=O.C(OCC)(=O)C.CCCCCC>CN(C=O)C>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([C@@H:21]2[CH2:20][CH2:19][C@@H:18]([C:36]3[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=3)[N:1]2[C:2]2[CH:3]=[CH:4][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[CH:6][CH:7]=2)=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 219047282-(4-Aminophenyl)-2-methylpropan-1-olHCID 58032014HCID 58032014, compound

Product 1

HCID 86649127HCID 86649127, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 194C (0.595 g, 3.60 mmole) was combined in DMF (3 mL) with (1R,4R)-1,4-bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate (0.259 g, 0.530 mmole), prepared as described in Example 37C, then heated overnight under nitrogen in an oil bath at 50° C. The reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was water washed (3×25 mL), dried over MgSO4, filtered and concentrated to an oil. Chromatography on silica gel eluting with ethyl acetate-hexane provided the title compound (0.0835 g, 34.1% yield) as an orange semi-solid.

Workup

  1. customprepared
  2. customThe reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. washwashed (3×25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-db6918ba36834332b6626b4a389dc510
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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