3,3,5-Trimethylcyclohexanol → 3,3,5-Trimethylcyclohexyl N-benzyloxycarbonyl-L-pyroglutamate

HRID 2254648Notes

Reaction equation

HRID 2254648 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[CH3:29][C:30]1([CH3:38])[CH2:35][CH:34]([CH3:36])[CH2:33][CH:32](O)[CH2:31]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH:32]1[CH2:33][CH:34]([CH3:36])[CH2:35][C:30]([CH3:38])([CH3:29])[CH2:31]1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 82983,3,5-TrimethylcyclohexanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Product 1

HCID 228451423,3,5-Trimethylcyclohexyl N-benzyloxycarbonyl-L-pyroglutamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

34.2 g (0.13 mol) of N-benzyloxycarbonyl-L-pyroglutamic acid (prepared according to Berichte 97, 2434 [1964] or Annalen 649, 183 [1961]) are added to 150 ml of dimethylformamide, followed by 2 g of dimethylaminopyridine and then 18.48 g (0.13 mol) of 3,3,5-trimethylcyclohexanol (mixture of 90% trans isomer and 10% cis isomer) diluted in 50 ml of dimethylformamide. 26.8 g (0.13 mol) of dicyclohexylcarbodiimide are then run in over a period of about 15 minutes, the reaction medium being kept at +5° C. The mixture is then stirred at room temperature for 24 hours, after which the solvent is evaporated off, the residue is taken up with dilute hydrochloric acid and extraction is carried out with chloroform.

Workup

  1. customare then run in over a period of about 15 minutes
  2. custombeing kept at +5° C
  3. customafter which the solvent is evaporated off
  4. extractionthe residue is taken up with dilute hydrochloric acid and extraction

Sources & evidence

ORD record
ord-98b25e5ddd9043a7b9f9fdad2f71d56a
Source dataset
uspto-grants-1993_08
Patent number
US05236946

Reaction notes

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