HCID 140407445, compound → tert-butyl N-(2-aminoethoxy)-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate

HRID 2228426Notes

Reaction equation

HRID 2228426 reaction equation
[C:1]([O:5][C:6]([N:8]([O:19][CH2:20][CH2:21][NH:22]C(OCC1C=CC=CC=1)=O)[C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[NH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O1CCCC1.[Pd]>[C:1]([O:5][C:6]([N:8]([O:19][CH2:20][CH2:21][NH2:22])[C:9]([NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[NH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 140407445HCID 140407445, compound

Product 1

HCID 140407450tert-butyl N-(2-aminoethoxy)-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamateYield 61%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [N,N′-di(tert-butoxycarbonyl)]2-(benzyloxycarbonylamino)ethoxyguanidine (0.73 g, 1.50 mmol), as prepared in the preceding step, 10% Pd/C (0.07 g) in ethanol (20 mL) and tetrahydrofuran (20 mL) was stirred under hydrogen (balloon) for 30 min. The catalysts were removed by filtration through Celite, the filtrate was concentrated in vacuo, and the residue was purified on a Waters silica Sep-Pak (5% methanol in dichloromethane saturated with ammonia) to give the title compound as a colorless oil (0.29 g, 61%). 1H-NMR (300 MHz, CDCl3) δ 9.08 (bs, 1H), 4.08 (t, J=5.2 Hz, 2H), 2.99 (q, J=5.1 Hz, 2H), 1.50 (s, 9H), 1.48 (s, 9H).

Workup

  1. customThe catalysts were removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue was purified on a Waters silica Sep-Pak (5% methanol in dichloromethane saturated with ammonia)

Sources & evidence

ORD record
ord-fc461d21122b4c8f97deb4375a894dd0
Source dataset
uspto-grants-2002_07
Patent number
US06417161B1

Reaction notes

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