HCID 67897689, compound → HCID 178511791, compound

HRID 476804Notes

Reaction equation

HRID 476804 reaction equation
CC(C)(OC([NH:7][C@H:8]([C:24]([NH:26][C@@H:27]([CH2:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1)[C@@H:28]([OH:43])[C:29]1[N:30](COCC2C=CC=CC=2)[CH:31]=[CH:32][N:33]=1)=[O:25])[CH2:9][C:10]1[N:14](COCC2C=CC=CC=2)[CH:13]=[N:12][CH:11]=1)=O)C.[H][H]>[OH-].[OH-].[Pd+2].CO.Cl>[CH:45]1([CH2:44][C@H:27]([NH:26][C:24](=[O:25])[C@H:8]([CH2:9][C:10]2[N:14]=[CH:13][NH:12][CH:11]=2)[NH2:7])[C@@H:28]([OH:43])[C:29]2[NH:33][CH:32]=[CH:31][N:30]=2)[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

6

Reactant 2

HCID 67897689HCID 67897689, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178511791HCID 178511791, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

A mixture of [(1,1-dimethylethoxy)carbonyl]-N-[(1S,2R)-1-(cyclohexylmethyl)-2-hydroxy-2-[1-[(phenylmethoxy)methyl]-1H-imidazol-2-yl]ethyl]-N3 -[(phenylmethoxy)methyl]-L-histidinamide (1.46 g., 2.0 mmole) [prepared as set forth in Example 11 (d)], 20% palladium hydroxide on carbon catalyst (350 mg.), and 1.0 N hydrochloric acid (4 ml., 4 mmole) in methanol (15 ml.) is hydrogenated under a slow stream of hydrogen for 20 hours at 25°, after which it is filtered and concentrated to dryness. The residue (1.1 g.) is dissolved in acetic acid (30 ml.) and dry HCl gas is bubbled through the solution for 30 minutes at 25°. The mixture is then stirred at 25° for 2 hours, after which is is concentrated in vacuo. The residue is triturated with acetonitrile to give 833 mg. of a white solid. The solid is dissolved in excess 1N hydrochloric acid and concentrated to dryness. The process is repeated three times to give N-[(1S,2R)-1-(cyclohexylmethyl)-2-hydroxy-2-(1H-imidazol-2-yl)ethyl]-L-histidinamide as a white solid.

Workup

  1. customprepared
  2. filtrationafter which it is filtered
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue (1.1 g.) is dissolved in acetic acid (30 ml.)
  5. customdry HCl gas is bubbled through the solution for 30 minutes at 25°
  6. concentrationafter which is is concentrated in vacuo
  7. customThe residue is triturated with acetonitrile
  8. customto give 833 mg
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-053926968e324e49bdcc9fae5ca1be17
Source dataset
uspto-grants-1989_12
Patent number
US04885292

Reaction notes

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