Triethylamine → 2-(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

HRID 1893030

Reaction equation

HRID 1893030 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[O:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]2[NH:16][CH2:15][CH:14]([OH:17])[CH2:13]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.FC1C([O:46][C:47](=O)[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][N:53]2[C:61](=[O:62])[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:54]2=[O:63])=C(F)C(F)=C(F)C=1F.CO.C(Cl)(Cl)Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[O:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]2[CH2:13][CH:14]([OH:17])[CH2:15][N:16]2[C:47](=[O:46])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][N:53]2[C:54](=[O:63])[C:55]3[C:60](=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:61]2=[O:62])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 593472896-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic Acid Pentafluorophenyl EsterHCID 1317282175-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-ol

Product 1

HCID 1317282162-(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Amine 38 (9.32 g, 22.2 mmol) and triethyl amine (4.55 g, 6.27 mL, 45 mmol) weres dissolved in anhydrous dichloromethane (20 mL) and cooled to 0° C. under argon. To that solution was added compound 43a (9.5 g, 22.2 mmol) at 0° C. The reaction mixture was brought to ambient temperature and stirred further. After 30 mins, disappearance of starting materials were ascertained by TLC. (10% MeOH/CHCl3). The reaction mixture was diluted with dichloromethane (100 mL) and washed with 5% NaOH solution (3×50 mL) followed by water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. Upon purification over silica gel compound 44a was obtained as foamy white solid in good yield. (13.2 g, 89%).

Workup

  1. customwas brought to ambient temperature
  2. washwashed with 5% NaOH solution (3×50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customUpon purification over silica gel compound 44a
  7. customwas obtained as foamy white solid in good yield

Sources & evidence

ORD record
ord-e17d66ae6db946faaa1be34cb076527e
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Linked notes

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