Water → N-[(2,4,6-Trimethoxyphenyl)methyl]-L-asparagine

HRID 2107849Notes

Reaction equation

HRID 2107849 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:20]([O:22]CC1C=CC=CC=1)=[O:21])[CH2:3][C:4](=[O:19])[NH:5][CH2:6][C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([O:13][CH3:14])=[CH:11][C:8]=1[O:9][CH3:10].O.CN(C=O)C>C(O)(=O)C>[CH3:18][O:17][C:16]1[CH:15]=[C:12]([O:13][CH3:14])[CH:11]=[C:8]([O:9][CH3:10])[C:7]=1[CH2:6][NH:5][C:4](=[O:19])[CH2:3][C@@H:2]([C:20]([OH:22])=[O:21])[NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 14836416HCID 14836416, compound

Product 1

HCID 14836418N-[(2,4,6-Trimethoxyphenyl)methyl]-L-asparagine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The fully protected derivative Z-Asn(Tmob)-OBzl prepared in Step 1 (2.0 g, 3.75 mmol) was dissolved in acetic acid (50 ml), water (14 ml) and DMF (10 ml) by slight warming and vigorous stirring, nitrogen was flushed through the low pressure hydrogenation flask, 5% palladium on carbon catalyst (400 mg) was added, and a gentle stream of hydrogen continuously passed over the vigorously stirred solution for 2 hours. Nitrogen was once more flushed through the system and the catalyst removed by filtration through a doubled fluted Whatman No. 1 filter paper. The filtrate was evaporated, the residue dried in vacuo, and triturated under ethyl acetate to give a white solid. The suspension was cooled overnight to 4 degrees, then filtered and washed with ethyl acetate. Yield after drying 1.16 g (96%), Rf 0.55 single spot n-butanol/acetic acid/water (3:1:1).

Workup

  1. customvigorous stirring, nitrogen was flushed through the low pressure hydrogenation flask, 5% palladium on carbon catalyst (400 mg)
  2. additionwas added
  3. customNitrogen was once more flushed through the system
  4. customthe catalyst removed by filtration through
  5. filtration1 filter paper
  6. customThe filtrate was evaporated
  7. customthe residue dried in vacuo
  8. customtriturated under ethyl acetate
  9. customto give a white solid
  10. temperatureThe suspension was cooled overnight to 4 degrees
  11. filtrationfiltered
  12. washwashed with ethyl acetate
  13. customYield
  14. dry with materialafter drying 1.16 g (96%), Rf 0.55 single spot n-butanol/acetic acid/water (3:1:1)

Sources & evidence

ORD record
ord-0aa7814b9d28400692098195b82ad524
Source dataset
uspto-grants-1990_06
Patent number
US04935536

Reaction notes

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