Citric Acid → HCID 86617541, compound

HRID 554147Notes

Reaction equation

HRID 554147 reaction equation
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O[C@@]1(C)C(=[N:21][C@H:22]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])C[C@H]2C[C@@H]1C2(C)C>O1CCCC1>[CH3:30][CH:23]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C@@H:22]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[NH2:21]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 67460297HCID 67460297, compound

Product 1

HCID 86617541HCID 86617541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 10% aqueous solution of citric acid (11 ml, 5.6 mmol) was added to a solution of 1-(1,1-dimethylethyl) 5-ethyl N-[(1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene]-3-methylglutamate (2 g) in tetrahydrofuran (10 ml) and the mixture was stirred at room temperature for 4 days. The mixture was the evaporated and the residue suspended in water (50 ml) and washed with diethyl ether (100 ml). The aqueous phase was then adjusted to pH˜7 using aqueous sodium hydrogen carbonate solution and then extracted with diethyl ether (3×100 ml). The organic fractions were combined, dried over sodium sulphate, filtered and evaporated to give 1-(1,1-dimethylethyl) 5-ethyl 3-methylglutamate (1.1 g) as a yellow oil which was used in the next step without further purification.

Workup

  1. customevaporated
  2. washwashed with diethyl ether (100 ml)
  3. extractionextracted with diethyl ether (3×100 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9dbd55940043440dad4aa7522ad3d718
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

Loading…