Triethylamine → Raloxifene

HRID 400096

Reaction equation

HRID 400096 reaction equation
[CH:1]1[C:6]([C:7]2[S:15][C:14]3[CH:13]=[C:12]([OH:16])[CH:11]=[CH:10][C:9]=3[C:8]=2[C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:24]=2)=[O:18])=[CH:5][CH:4]=[C:3]([OH:34])[CH:2]=1.Cl.C(N(CC)CC)C.CC/C=C/C/C=C/C/C=C/CCCCCCCC(Cl)=O>CN(C1C=CN=CC=1)C.C1COCC1>[CH:5]1[C:6]([C:7]2[S:15][C:14]3[CH:13]=[C:12]([OH:16])[CH:11]=[CH:10][C:9]=3[C:8]=2[C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=2)=[O:18])=[CH:1][CH:2]=[C:3]([OH:34])[CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 54900Raloxifene HydrochlorideHCID 5702742Linolenoyl chloride

Product 1

HCID 5035Raloxifene

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

This derivative was prepared in a manner similar to Example 1, using 2.6 g (0.005 mol) of Raloxifene HCl, 2 g (0.02 mol) of triethylamine, 20 mg of DMAP, and 3.2 g (0.01 mol) of linolenoyl chloride in 250 mL of THF. The final product was chromatographed on a silica gel column eluted with EtOAc-hexane (8:2). This yielded 3.21 g of the title compound as clear oil.

Workup

  1. customThis derivative was prepared in a manner similar to Example 1
  2. customThe final product was chromatographed on a silica gel column
  3. washeluted with EtOAc-hexane (8:2)

Sources & evidence

ORD record
ord-11270f0c82814a45b7a68d7d0fc374dd
Source dataset
uspto-grants-1998_10
Patent number
US05827844

Linked notes

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