Sodium → HCID 178448650, compound

HRID 733226Notes

Reaction equation

HRID 733226 reaction equation
[Na].[Cl-].[NH2:3][C:4]([NH2:6])=[NH2+:5].[C:7]([C:11]1[CH:19]=[C:18]2[C:14]([C:15](=[O:30])[N:16]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH:17]2[CH2:20][C:21](OCC)=[O:22])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8]>C(O)C>[C:7]([C:11]1[CH:19]=[C:18]2[C:14]([C:15](=[O:30])[N:16]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH:17]2[CH2:20][C:21]([NH:5][C:4]([NH2:6])=[NH:3])=[O:22])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 5460839Carbamimidoylazanium ChlorideHCID 69714217ethyl (6-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

Product 1

HCID 178448650HCID 178448650, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

N-[(6-tert-Butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 9, starting with 20 cm3 of absolute ethanol, 0.37 g of sodium, 1.56 g of guanidinium chloride and 3.53 g of ethyl (6-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 10 cm3 of absolute ethanol. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours and is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in a mixture of 15 cm3 of water and 45 cm3 of diethyl ether and then stirred at a temperature in the region of 0° C. for 2 hours. The precipitate obtained is filtered off, washed with twice 10 cm3 of ice-cold water and then dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C. 2.5 g of N-[(6-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are thus obtained in the form of a brown powder melting at 214-215° C. Mass spectrum: DCI: m/e 345 (M+H)+.

Workup

  1. customN-[(6-tert-Butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared
  2. concentrationis then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. additionThe residue is taken up in a mixture of 15 cm3 of water and 45 cm3 of diethyl ether
  4. stirringstirred at a temperature in the region of 0° C. for 2 hours
  5. customThe precipitate obtained
  6. filtrationis filtered off
  7. washwashed with twice 10 cm3 of ice-cold water
  8. customdried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-db15b88df2ea4a0fb7955b728816b44d
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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