N,N'-Di-Boc-thiourea → HCID 178463305, compound

HRID 2122013Notes

Reaction equation

HRID 2122013 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([CH3:27])[C:7](=[C:9]3[S:13][C:12](=[N:14][C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[NH:23][CH2:24][CH3:25])[C:18]#[N:19])[NH:11][C:10]3=[O:26])[S:8][C:4]=2[CH:3]=1.[C:30]([O:34][C:35]([NH:37][C:38]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=S)=[O:36])([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C.C(Cl)(Cl)Cl.Cl[Hg]Cl>[CH2:18]([N:11]1[C:10](=[O:26])[C:9](=[C:7]2[N:6]([CH3:27])[C:5]3[CH:28]=[CH:29][C:2]([NH:1][C:38]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:37][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])=[CH:3][C:4]=3[S:8]2)[S:13][C:12]1=[N:14][C:15]1[CH:16]=[C:17]([C:18]#[N:19])[CH:20]=[CH:21][C:22]=1[NH:23][CH2:24][CH3:25])[C:17]1[CH:20]=[CH:21][CH:22]=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 5193990N,N'-Di-Boc-thioureaHCID 136377672HCID 136377672, compound

Product 1

HCID 178463305HCID 178463305, compoundYield 173.1%

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of the product of Example 272 (77 mg, 0.15 mmol), N,N′-di-(tert-butoxycarbonyl)thiourea (50 mg, 0.18 mmol) and TEA (70 μL, 0.5 mmol) in anhydrous DMF (1.5 mL) at 0° C. was added HgCl2 (49 mg, 0.18 mmol). The resulting mixture was stirred at 0° C. for 30 min, then at ambient temperature overnight. The mixture was diluted with CHCl3, washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with MeOH-DCM (0:100 to 20:80) to afford the title compound (98 mg, 87%). 1H-NMR (CDCl3): δ 11.62 (1H, br s), 10.43 (1H, br s), 8.02 (2H, m), 7.45-7.20 (7H, m), 7.02 (1H, d), 6.49 (1H, t), 5.16 (2H, s), 3.82 (3H, s), 3.04-2.96 (2H, m), 1.43 (9H, s), 1.35 (9H, s), 1.02 (3H, t); MS(ESI): 756 (MH+).

Workup

  1. customat ambient temperature
  2. customovernight
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with MeOH-DCM (0:100 to 20:80)

Sources & evidence

ORD record
ord-5e25374c62bf4ee390346b9107b6687c
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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