Triethylamine → tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

HRID 963552Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=S)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21](CC)CC)C>CN(C=O)C.C(OCC)(=O)C.Cl[Hg]Cl>[C:6]([NH:8][C:9](=[NH:21])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of amine 228 (126 mg, 0.42 mmol), N,N'-bis-tert-butoxycarbonylthiourea (127 mg, 0.46 mmol), and triethylamine (123 μL, 0.88 mmol) in DMF (4 mL) at 0° C. was added HgCl2 (125 mg, 0.46 mmol). The mixture was stirred at 0° C. for 30 min and at room temperature for 1.5 h. The reaction was diluted with ethyl acetate and filtered through celite. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with saturated NaCl, dried (MgSO4), filtered and the solvent was evaporated. The crude product was purified on silica gel (2/1, 1/1-hexane/ethyl acetate) to afford bis-Boc-guanidine 251 (155 mg, 69%) as a solid: 1H NMR (CDCl3) δ11.40 (s, 1H), 8.66 (d, 1H, J=7.9), 6.8 (s, 1H), 6.22 (d, 1H, J=8.9), 4.43-4.34 (m, 1H), 4.19-4.08 (m, 1H), 4.03 (m, 1H), 3.76 (s, 3H), 3.35 (m, 1H), 2.79 (dd, 1H, J=5.4, 17.7), 2.47-2.36 (m, 1H), 1.92 (s, 3H), 1.50, 1.49 (2 s, 18H), 0.89 (m, 6H).

Workup

filtrationfiltered through celite
customThe solvent was evaporated
customthe residue was partitioned between ethyl acetate and water
washThe organic phase was washed with saturated NaCl
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was evaporated
customThe crude product was purified on silica gel (2/1, 1/1-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-4a3227f885fc44d7a714564ef1798e61
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763483

Reaction notes

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