Hydrochloric Acid → N-(Triphenylmethyl)-L-glutamine

HRID 1110193Notes

Reaction equation

HRID 1110193 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[H][H].C(N(CC)CC)C>[Pd].O.CO>[NH2:1][C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10962399Z-Gln(Trt)-OHHCID 178418361HCID 178418361, compound

Product 1

HCID 7408404N-(Triphenylmethyl)-L-glutamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A suspension of 10.4 g of Z-Gln(Trt)-OH (20 mmol) in 180 ml of a 9:1 mixture of methanol and water and 20 ml of one-normal aqueous hydrochloric acid is hydrogenated at room temperature and under atmospheric pressure in the presence of 0.5 g of a 10% palladium on charcoal catalyst; after the uptake of hydrogen is complete the starting material has dissolved. The catalyst is filtered off and washed with methanol; the filtrate is concentrated to 200 g and, at 60°, 2.8 ml of triethylamine (20 mmol) are added, whereupon the product immediately starts to crystallize. The mixture is concentrated to 100 g and left to stand at about 4° for some time, and the crystals are filtered off and washed with a mixture of methanol and water until free of chloride. The H-Gln(Trt)-OH obtainable in this way contains 0.5 mole of water and melts at 233° (with decomposition).

Workup

  1. dissolutionhas dissolved
  2. filtrationThe catalyst is filtered off
  3. washwashed with methanol
  4. concentrationthe filtrate is concentrated to 200 g and, at 60°
  5. customto crystallize
  6. concentrationThe mixture is concentrated to 100 g
  7. waitleft
  8. customto stand at about 4° for some time
  9. filtrationthe crystals are filtered off
  10. washwashed with a mixture of methanol and water until free of chloride

Sources & evidence

ORD record
ord-6da42452493d46829f89a0603a6cd755
Source dataset
uspto-grants-1994_06
Patent number
US05324833

Reaction notes

Loading…