HCID 87947717, compound → HCID 9893043, compound

HRID 1597307Notes

Reaction equation

HRID 1597307 reaction equation
[NH2:1][C:2](=[N:34]O)[C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([CH3:33])[C:13](=[O:14])[N:12]([CH2:15][C:16]([NH:18][C@H:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[C:11](=[O:32])[NH:10]2)=[CH:5][CH:4]=1.[H][H]>C(O)(=O)C.[Pd]>[C:21]([OH:23])(=[O:22])[CH3:20].[NH2:34][C:2](=[NH:1])[C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([CH3:33])[C:13](=[O:14])[N:12]([CH2:15][C:16]([NH:18][C@H:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[C:11](=[O:32])[NH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 87947717HCID 87947717, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9893043HCID 9893043, compoundYield 168.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

11 kg (22.869 mol) of ethyl (S)-3-(2-((S)-4-(4-(amino-hydroximino-methyl)-phenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetylamino)-3-phenyl-propionate were dissolved in 70 l of glacial acetic acid and this solution was introduced into a 125 l autoclave. A suspension of 1.0 kg of palladium/charcoal (10%; 50% water) and 5 l of glacial acetic acid was added to the solution. The mixture was hydrogenated for 15 h at 50° C. and 10 bar hydrogen pressure. The catalyst was filtered off with suction through a pressure filter under nitrogen and washed with 5 l of glacial acetic acid. The filtrate was completely evaporated in vacuo on a rotary evaporator at a bath temperature of 60° C. The residue was dissolved in 30 l of acetone and the solution was added, over 30 min and at 20° C., to 200 l of methyl tert-butyl ether. The mixture was subsequently stirred at room temperature for 1 h and the precipitated product was centrifuged. The filter cake was subsequently washed with 10 l of methyl tert-butyl ether, removed from the centrifuge and dried in vacuo. 10.1 kg (85%) of product were obtained. FAB-MS: 466 (M+H)+

Workup

  1. additionthis solution was introduced into a 125 l autoclave
  2. additionwas added to the solution
  3. filtrationThe catalyst was filtered off with suction through a pressure
  4. filtrationfilter under nitrogen
  5. washwashed with 5 l of glacial acetic acid
  6. customThe filtrate was completely evaporated in vacuo on a rotary evaporator at a bath temperature of 60° C
  7. dissolutionThe residue was dissolved in 30 l of acetone
  8. additionthe solution was added, over 30 min and at 20° C., to 200 l of methyl tert-butyl ether
  9. washThe filter cake was subsequently washed with 10 l of methyl tert-butyl ether
  10. customremoved from the centrifuge
  11. customdried in vacuo

Sources & evidence

ORD record
ord-bc7bcc8d6ac74e029add6ce8153018f2
Source dataset
uspto-grants-2001_09
Patent number
US06294562B1

Reaction notes

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