Nitrogen → HCID 10837709, compound

HRID 2221421Notes

Reaction equation

HRID 2221421 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].N#N>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]([NH:13][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[N:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 24758Sodium hydrideHCID 13783255110065-79-92×

Product 1

HCID 10837709HCID 10837709, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product was prepared as described in J.O.C., 1998, 63 (23), 8432-8439, starting from a solution of N,N′-bis(benzyloxycarbonyl)guanidine (prepared as described in J.O.C., 1998, 63 (23), 8432-8439), (3 g, 9.17 mmol) in anhydrous THF which was brought to T=−45° C., after which NaH (60% in mineral oil, 728 mg, 18.1 mmol) was added piecemeal in small portions. The suspension was kept at T=−45° C. for 1 hour after which benzylchloroformiate (1.55 g, 9.17 mmol) was added and the suspension was brought back to room temperature in an N2 atmosphere and left under stirring for 18 hours. The mixture was concentrated at reduced pressure, and then diluted with CH2Cl2 and H2O; the two phases were separated, the organic phase was washed with HCl 1N, NaCl s.s. and dried on anhydrous Na2SO4. The crude reaction product was purified by silica gel chromatography using CH2Cl2/Et2O as eluent to give 810 mg of product (yield: 19%). Analytical data as reported in the literature.

Workup

  1. customThe product was prepared
  2. customwas brought to T=−45° C.
  3. additionafter which benzylchloroformiate (1.55 g, 9.17 mmol) was added
  4. waitleft
  5. concentrationThe mixture was concentrated at reduced pressure
  6. additiondiluted with CH2Cl2 and H2O
  7. customthe two phases were separated
  8. washthe organic phase was washed with HCl 1N, NaCl s.s
  9. dry with materialand dried on anhydrous Na2SO4
  10. customThe crude reaction product
  11. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-48a14df1de224784ba7aafdecb7429f6
Source dataset
uspto-grants-2008_05
Patent number
US07368605B2

Reaction notes

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