Isopropanol → 3-[[2-amino-1-oxo-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl]amino]-2-hydroxy-5-methylhexanoic acid, 1-methylethyl ester

HRID 846468Notes

Reaction equation

HRID 846468 reaction equation
[OH:1][CH:2]([CH:6]([NH:11][C:12](=[O:50])[CH:13]([NH:39]C(OCC1C=CC=CC=1)=O)[CH2:14][C:15]1[N:16]=[CH:17][N:18]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])[C:3]([OH:5])=[O:4].[H][H].[CH:53](O)([CH3:55])[CH3:54]>[Pd]>[NH2:39][CH:13]([CH2:14][C:15]1[N:16]=[CH:17][N:18]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:19]=1)[C:12]([NH:11][CH:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH:2]([OH:1])[C:3]([O:5][CH:53]([CH3:55])[CH3:54])=[O:4])=[O:50]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 198845362-hydroxy-5-methyl-3-[[1-oxo-2[[(phenylmethoxy)carbonyl]amino]-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl]amino]hexanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 572117653-[[2-amino-1-oxo-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl]amino]-2-hydroxy-5-methylhexanoic acid, 1-methylethyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Palladium on charcoal, 10%, 1 g, is added to 11.8 g (16.5 mmol) of 2-hydroxy-5-methyl-3-[[1-oxo-2[[(phenylmethoxy)carbonyl]amino]-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl]amino]hexanoic acid (mixture of [2R-[2R*,3S*(S*)]] and [2S-[2R*,3R*(R*)]]isomers) dissolved in isopropanol and the mixture is exposed to hydrogen gas. After complete uptake of hydrogen the mixture is filtered, the solvent evaporated in vacuo and the residue co-evaporated with diethyl ether to give 9.5 g of the title compound as a beige foam after drying under high vacuum for one hour.

Workup

  1. filtrationAfter complete uptake of hydrogen the mixture is filtered
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-d8e55f11bde54cb5ac97b9e46cc99ecc
Source dataset
uspto-grants-1992_08
Patent number
US05135914

Reaction notes

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