Dimethylformamide → HCID 140401819, compound

HRID 619394Notes

Reaction equation

HRID 619394 reaction equation
[C:1]([NH:8][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=S)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:19][CH2:20]N(CC)CC.C[N:27](C=O)C>CO.[Pd].Cl[Hg]Cl>[CH2:19]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[NH:27])[CH3:20]

Participants

7

Reactant 3

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 5193990N,N'-Di-Boc-thiourea

Product 1

HCID 140401819HCID 140401819, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24085Mercuric ChlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 211 (100 mg, 0.38 mmol) in methanol was treated with 10% Pd-C (50 mg) and was shaken under 60 psi H2 in a Paar apparatus. The catalyst was filtered (celite) and solvent was evaporated to afford a solid residue which was dissolved in DMF (2.5 mL). To this solution was added bis-Boc-thiourea (113 mg, 0.42 mmol), and Et3N (111 mL, 0.80 mmol). The DMF solution was cooled to 0° C., HgCl2 (114 mg, 0.42 mmol) was added, and the mixture was stirred at 0° C. for 3 h then at rt for 20 h. The crude product was isolated in the same manner as described for Example 201 and was chromatographed on silica gel (1/1-ethyl acetate/hexane) to afford bis-Boc-guanidine 212 (145 mg, 79%) as a colorless glass: 1H NMR (300 MHz, CDCl3) d 1.25 (t, 3H, J=7.6), 1.49 (s, 9H), 1.55 (s, 9H), 2.16 (s, 3H), 2.68 (q, 2H, J=7.6), 3.91 (s, 3H), 7.86 (d, 1H, J=1.5), 8.05 (d, 1H, J=1.5), 8.76 (s, 1H), 10.46 (s, 1H), 11.54 (s, 1H).

Workup

  1. filtrationThe catalyst was filtered (celite) and solvent
  2. customwas evaporated
  3. customto afford a solid residue which
  4. stirringthe mixture was stirred at 0° C. for 3 h
  5. customThe crude product was isolated in the same manner
  6. customwas chromatographed on silica gel (1/1-ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f1a6777f69ba4745bafd750d046dc8aa
Source dataset
uspto-grants-1999_09
Patent number
US05958973

Reaction notes

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