Acetic Acid → Toremifene

HRID 2297330Notes

Reaction equation

HRID 2297330 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1)[CH3:3].[C:30]([OH:33])(=[O:32])[CH3:31]>CO>[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[CH2:15][CH2:16][Cl:17])=[CH:11][CH:12]=1)[CH3:3].[C:30]([O-:33])(=[O:32])[CH3:31].[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[CH2:15][CH2:16][Cl:17])=[CH:11][CH:12]=1)[CH3:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3005573Toremifene

Product 2

HCID 3005573ToremifeneHCID 131723673HCID 131723673, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of toremifene base (1.00 g, 0.0025 moles) and methanol (20 ml) was slowly added acetic acid (160 μl, 0.0028 moles). The mixture was stirred for a while and evaporated to dryness. The acetate of toremifene was obtained as sticky white solid. 1H-NMR (d4-MeOH) d 7.37 (tt, 2H), 7.33-7.25 (m, 3H), 7.25-7.10 (m, 5H), 6.82 (dt, 2H), 6.63 (dt, 2H), 4.08 (t, 2H), 3.39 (t, 2H), 3.09 (t, 2H), 2.89 (t, 2H), 2.60 (s, 6H), 1.92 (s, 3H).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-eecbc83b29864c5798b3604288828541
Source dataset
uspto-grants-2002_12
Patent number
US06491951B1

Reaction notes

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