1,2-Dichloroethane → HCID 11445050, compound

HRID 1295865Notes

Reaction equation

HRID 1295865 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8](=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:4]1.[C:29]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:41]=1[O:42][CH3:43])[C:36](O)=[O:37])([CH3:32])([CH3:31])[CH3:30].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:12][CH2:11][CH2:10][CH2:9][C:8]([N:5]2[CH2:6][CH2:7][CH:3]([CH2:2][NH:1][C:36](=[O:37])[C:35]3[CH:39]=[C:40]([C:44]([CH3:45])([CH3:46])[CH3:47])[C:41]([O:42][CH3:43])=[C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:34]=3)[CH2:4]2)=[O:28])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 22324252HCID 22324252, compoundHCID 58911294HCID 58911294, compound

Product 1

HCID 11445050HCID 11445050, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-aminomethyl-pyrrolidin-1-yl)-6,6-bis-(4-fluoro-phenyl)-hexan-1-one (0.49 g, 1.26 mmol) in dry CH2Cl2 (35 ml) was added 3,5-di-tert-butyl-4-methoxy benzoic acid (0.33 g, 1.26 mmol) under nitrogen. To the reaction was added EDC (0.48 g, 2.52 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue dissolved in ethyl acetate: water (10:1) (130 ml). The organic was washed with water (30 ml, 2×) and 10% NaOH (30 ml) and dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2:CH3OH (15:1) to give a desired product in good yield.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue dissolved in ethyl acetate: water (10:1) (130 ml)
  3. washThe organic was washed with water (30 ml, 2×) and 10% NaOH (30 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-02bb372733d44eb0905cb1127104593d
Source dataset
uspto-grants-2007_07
Patent number
US07244758B2

Reaction notes

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