Triethylamine → (S,S)-2,4-dibenzylglutaric acid

HRID 1493439Notes

Reaction equation

HRID 1493439 reaction equation
[CH2:1]([C@@H:8]([CH2:12][C@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>C(O)(C)C>[CH2:1]([C@H:8]([CH2:12][C@@H:13]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 14557653(R*,R*)-2,4-dibenzylglutaric acid

Product 1

HCID 14557654(S,S)-2,4-dibenzylglutaric acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

The chiral (S,S)-2,4-dibenzylglutaric acid is prepared as follows: To 5.0 g of (R*,R*)-2,4-dibenzylglutaric acid in 20 ml of isopropanol is added 0.81 g of triethylamine and the mixture is stirred for 20 minutes. To this mixture is added 0.97 g of d(+)-alpha-methylbenzylamine in 20 ml of isopropanol and the solution is stirred overnight. The solid is collected and recrystallized twice from isopropanol to yield (S,S)-2,4-dibenzylglutaric acid as the d(+)-alpha-methylbenzylamine salt melting at 201°-203°; [alpha]D =-20.4° (c=1 in methanol). To a warm solution of the above salt in 70 ml of water and 30 ml of ethanol is added 1 ml of concentrated hydrochloric acid. After standing 24 hours the solid is collected, washed with water and dried to yield (S,S)-2,4-dibenzylglutaric acid melting at 150°-152°; [alpha]D =+8.9° (c=2.0 in methanol).

Workup

  1. customThe chiral (S,S)-2,4-dibenzylglutaric acid is prepared
  2. stirringthe solution is stirred overnight
  3. customThe solid is collected
  4. customrecrystallized twice from isopropanol

Sources & evidence

ORD record
ord-9938c583a96a47ae84ff70871de5a43e
Source dataset
uspto-grants-1991_06
Patent number
US05021430

Reaction notes

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