Hydrochloric Acid → HCID 178512190, compound

HRID 2221422Notes

Reaction equation

HRID 2221422 reaction equation
C(OC([N:8]=[C:9]([N:16](C(OC(C)(C)C)=O)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=O)(C)(C)C.Cl>CCO>[NH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]([NH:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)=[NH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178454266HCID 178454266, compound

Product 1

HCID 178512190HCID 178512190, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product was prepared starting from 4-[N2,N3-bis(ter-butoxycarbonyl)-N3-(4-fluorobenzyl)-guanidino]-1-aminobutane (116 mg, 0.26 mmol) solubilised in EtOH (1.5 ml). Every 2 hours 1 ml of HCl 12 N was added; after 4 hours, the solution was left for 15 min at room temperature, and then brought to T=55° C. and kept at that temperature for 6 hours. The solution was concentrated at reduced pressure and the residual aqueous phase was washed with CH2Cl2 and AcOEt. The aqueous phase was concentrated to dryness in vacuo, giving 46 mg of product as a yellow oil (yield: 57%). 1H-NMR (CD3OD) δ 7.31-7.24 (2H, m), 7.03-7.12 (2H, m), 4.34 (2H, s), 3.26 (2H, t), 3.17 (2H, t), 1.58-1.53 (2H, m).

Workup

  1. customThe product was prepared
  2. waitthe solution was left for 15 min at room temperature
  3. custombrought to T=55° C.
  4. waitkept at that temperature for 6 hours
  5. concentrationThe solution was concentrated at reduced pressure
  6. washthe residual aqueous phase was washed with CH2Cl2 and AcOEt
  7. concentrationThe aqueous phase was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-e1f28d8d7090463c9f27178a452c59ba
Source dataset
uspto-grants-2008_05
Patent number
US07368605B2

Reaction notes

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