Hydrogen chloride-ethyl acetate → HCID 86755913, compound

HRID 366051Notes

Reaction equation

HRID 366051 reaction equation
[C:1]([CH:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH2:10][CH2:11][NH2:12])[NH2:8])(=[O:3])[NH2:2].[ClH:22].CCOC(C)=O>CO>[C:1]([CH:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH2:10][CH2:11][NH2:12])[NH2:8])(=[O:3])[NH2:2].[ClH:22].[C:1]([CH:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH2:10][CH2:11][NH2:12])[NH2:8])(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86755913HCID 86755913, compound2×

Product 2

HCID 86755913HCID 86755913, compoundHCID 86755914HCID 86755914, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of(R)-N2 -(Boc)-N5 -(Cbz)-(R or S)-N-[1-carbamoyl-(4-methoxy-phenyl)methyl]ornithine amide and (R)-N2 -(Boc)-N5 -(Cbz)-(S or R)-N-[1-carbamoyl(4-methoxyphenyl)methyl]ornithine amide (4.5 g; 8.5 mmol) was dissolved in 25 mL of MeOH and 100 mL of HCl/EtOAc was added. The mixture was magnetically stirred at room temperature for 1 hour, then evaporated at reduced pressure to give a crude hydrochloride salt of the diastereomers of (R)-N5 -(Cbz)-(R or S)-N-[1-carbamoyl-(4-methoxy-phenyl)methyl]ornithine amide and (R)-N5 -(Cbz)-(S or R)-N-[1 -carbamoyl-(4-methoxyphenyl)methyl]ornithine amide hydrochloride. Crystallization from MeOH:EtOAc provided 1.3 g of the more polar sub-title diastereomer (32%).

Workup

  1. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-14ff06371899488daf861211d2267ae9
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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