1-benzyl 5-tert-butyl (1S)-{1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]pentamethylene}biscarbamate → HCID 86597898, compound

HRID 459645Notes

Reaction equation

HRID 459645 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[NH:8][C:9]([C@@H:11]([NH:24]C(=O)OCC1C=CC=CC=1)[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:10]>CO.[Pd]>[NH2:24][C@H:11]([C:9]([NH:8][C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH2:1])=[O:10])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 1

HCID 865978971-benzyl 5-tert-butyl (1S)-{1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]pentamethylene}biscarbamate

Product 1

HCID 86597898HCID 86597898, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the crude product of 1-benzyl 5-tert-butyl (1S)-{1-[(5-amino-1-methyl-1H-pyrazol-4-yl)carbamoyl]pentamethylene}biscarbamate in methanol (350 ml) was treated with 10% palladium on carbon (2.0 g) under a hydrogen atmosphere at room temperature for 6 days. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give tert-butyl (5S)-5-amino-6-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-6-oxohexylcarbamate (12.1 g) as a solid.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated with ethyl acetate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-40c426e7d3ab472fb1008faefa77171e
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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