[N,N'-di(tert-butoxycarbonyl)]3-(benzyloxycarbonylamino)-1-propoxyguanidine → [N,N'-Di(tert-butoxycarbonyl)]3-amino-1-propoxyguanidine

HRID 1700311Notes

Reaction equation

HRID 1700311 reaction equation
[C:1]([O:5][C:6]([N:8]([O:30][CH2:31][CH2:32][CH3:33])[C:9]([N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:12]C(OCC1C=CC=CC=1)=O)=[NH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O1CCCC1.[Pd]>[C:1]([O:5][C:6]([N:8]([O:30][CH2:31][CH2:32][CH3:33])[C:9]([N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH2:12])=[NH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 18408946[N,N'-di(tert-butoxycarbonyl)]3-(benzyloxycarbonylamino)-1-propoxyguanidine

Product 1

HCID 18408947[N,N'-Di(tert-butoxycarbonyl)]3-amino-1-propoxyguanidineYield 28.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [N,N′-di(tert-butoxycarbonyl)]3-(benzyloxycarbonylamino)-1-propoxyguanidine (760 mg, 1.7 mmol), as prepared in the preceding step, and 10% Pd/C (80 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, the filtrate was concentrated in vacuo, and 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 (160 mg, 28%). 1H-NMR (300 MHz, CDCl3) δ4.12 (t, J=6.1 Hz, 2H), 2.85 (t, J=6.7 Hz, 2H), 1.84 (pentet, J=6.2 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-5b99c954229f42959a3c9c2bd3e9127c
Source dataset
uspto-grants-2002_02
Patent number
US06350764B2

Reaction notes

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