Water → HCID 7408430, compound

HRID 2209861Notes

Reaction equation

HRID 2209861 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:28]([OH:30])=[O:29])[CH2:3][CH2:4][C:5](=[O:27])[NH:6][C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1.O>CO.Cl.[Pd]>[NH2:1][C@H:2]([C:28]([OH:30])=[O:29])[CH2:3][CH2:4][C:5](=[O:27])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 962WaterHCID 90470049N-[(4-Methylphenyl)diphenylmethyl]-N2-[(phenylmethoxy)carbonyl]-L-glutamine

Product 1

HCID 7408430HCID 7408430, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of 107.3 g Z-Gln(Mtt)OH (200 mM) in 800 ml methanol and 200 ml IN hydrochloric acid is hydrogenated at room temperature and normal pressure in the presence of 0.4 g palladium on carbon (10%) catalyst. On completion of the hydrogen uptake the catalyst is filtered off, washed with methanol and the filtrate, after addition of 27.9 ml triethylamine (200 mM) and 200 ml water, concentrated to a volume of about 600 ml. The formed crystalline precipitate is filtered off and washed with water until the washings are chloride-free. The obtained H-Gln(Mtt)OH contains 0.5-1 mole water and decomposes slowly above 231° C. Yield 85%.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationOn completion of the hydrogen uptake the catalyst is filtered off
  3. washwashed with methanol
  4. additionthe filtrate, after addition of 27.9 ml triethylamine (200 mM) and 200 ml water
  5. concentrationconcentrated to a volume of about 600 ml
  6. filtrationThe formed crystalline precipitate is filtered off
  7. washwashed with water until the washings
  8. customdecomposes slowly above 231° C

Sources & evidence

ORD record
ord-66c4307aa86b453bb77f61fbf565f916
Source dataset
uspto-grants-1995_10
Patent number
US05455363

Reaction notes

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