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

HRID 619393Notes

Reaction equation

HRID 619393 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].CC[N:21](CC)CC>CN(C=O)C.Cl[Hg]Cl>[C:6]([NH:8][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[NH:21])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 5193990N,N'-Di-Boc-thiourea

Product 1

HCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamateYield 55.2%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 205 (340 mg, 1.6 mmol), N,N'-bis-tert-butoxycarbonylthiourea (442 mg, 1.6 mmol, prepared according to literature procedure: Synthetic Commun.1993, 23, 1443.), and Et3N (292 mL, 3.36 mmol) in DMF (4 mL) at 0° C. was added HgCl2 (478 mg, 1.76 mmol) and the mixture was allowed to warm to rt overnight, stirring a total of 20 h. The crude product was isolated in the same manner as described in Example 201 and the was chromatographed on silica gel (5% ethyl acetate/dichloromethane) to afford bis-Boc-guanidine 206 (229 mg, 31%) as a pale orange solid: 1H NMR (300 MHz, CDCl3) d 1.49 (s, 9H), 1.54 and 1.56 (2s, 18H), 4.48 (br s, 2H, NOE observed for C-4 NH2 and C-3 H), 6.73 (d, 1H, J=8.4), 7.68 (dd, 1H, J=1.6, 8.4), 7.86 (s, 1H), 9.96 (s, 1H), 11.64 (s, 1H).

Workup

  1. customThe crude product was isolated in the same manner
  2. customthe was chromatographed on silica gel (5% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-1717ee83f3074843a583c6c64ed9082d
Source dataset
uspto-grants-1999_09
Patent number
US05958973

Reaction notes

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