Water → N-[(4-Methylphenyl)diphenylmethyl]-L-asparagine

HRID 2209859Notes

Reaction equation

HRID 2209859 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][C:4](=[O:26])[NH:5][C:6]([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:7]1[CH:13]=[CH:12][C:10]([CH3:11])=[CH:9][CH:8]=1.O>CO.Cl.[Pd]>[NH2:1][C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][C:4](=[O:26])[NH:5][C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]1[CH:8]=[CH:9][C:10]([CH3:11])=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 962WaterHCID 56845350N~2~-[(Benzyloxy)carbonyl]-N-[(4-methylphenyl)(diphenyl)methyl]-L-asparagine

Product 1

HCID 7408426N-[(4-Methylphenyl)diphenylmethyl]-L-asparagineYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of 52.3 g Z-Asn(Mtt)OH (100 mM) in 400 ml methanol and 100 ml IN hydrochloric acid is hydrogenated at room temperature and normal pressure in the presence of 2 g of a palladium on carbon (10%) catalyst. On completion of hydrogen uptake the catalyst is filtered off, washed with methanol and the filtrate, after addition of 13.9 ml triethylamine (100 mM) and 100 ml water, condensed in vacuo to a volume of about 300 ml. The crystalline precipitate is collected by filtration and washed with water until the washings are chloride-free. The obtained H-Asn(Mtt)OH contains 0.5-1 mole of water and decomposes above 222° C. Yield 80%.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationOn completion of hydrogen uptake the catalyst is filtered off
  3. washwashed with methanol
  4. additionthe filtrate, after addition of 13.9 ml triethylamine (100 mM) and 100 ml water, condensed in vacuo to a volume of about 300 ml
  5. filtrationThe crystalline precipitate is collected by filtration
  6. washwashed with water until the washings
  7. customdecomposes above 222° C

Sources & evidence

ORD record
ord-19cfc153b652449089fc7bb992530fcd
Source dataset
uspto-grants-1995_10
Patent number
US05455363

Reaction notes

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