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

HRID 1796434Notes

Reaction equation

HRID 1796434 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 (730 mg, 1.5 mmol), as prepared in the preceding step, and 10% Pd/C (70 mg) in ethanol (20 mL) and tetrahydrofuran (20 mL) was hydrogenated under hydrogen (balloon) for 30 min. The catalyst was removed by filtration through Celite and the filtrate was concentrated in vacuo. The residue was purified by Waters Sep-Pak (10 g, 95:5 methylene chloride: methanol saturated with ammonia) to give the title compound as a colorless oil (290 mg, 61%). 1H-NMR (300 MHz, CDCl3) δ 9.08 (br s, 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 catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by Waters Sep-Pak (10 g, 95:5 methylene chloride: methanol saturated with ammonia)

Sources & evidence

ORD record
ord-6d8ea26d5d1340a68f62513aa750a4b4
Source dataset
uspto-grants-2006_04
Patent number
US07029654B2

Reaction notes

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