Hydrochloric Acid → HCID 69422026, compound

HRID 1354838Notes

Reaction equation

HRID 1354838 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15]C(OC(C)(C)C)=O)[CH2:12][N:11]([C:23]2[C:32]([N:33]3[CH2:38][C@@H:37]([NH:39]C(OC(C)(C)C)=O)[CH2:36][C@@H:35]([NH:47]C(OC(C)(C)C)=O)[CH2:34]3)=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([N+:55]([O-])=O)[CH:29]=3)[N:24]=2)[CH2:10]1)=O)(C)(C)C.Cl>C(O)(C(F)(F)F)=O.CO>[NH2:15][C@@H:13]1[CH2:14][C@H:9]([NH2:8])[CH2:10][N:11]([C:23]2[C:32]([N:33]3[CH2:34][C@@H:35]([NH2:47])[CH2:36][C@@H:37]([NH2:39])[CH2:38]3)=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([NH2:55])[CH:29]=3)[N:24]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58865534HCID 58865534, compound

Product 1

HCID 69422026HCID 69422026, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2,3-Bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-6-nitro-quinoxaline (245) (0.05 g, 0.135 mmol) was dissolved in TFA (3 mL) and the mixture was shaken at room temperature in a Teflon septum capped vial for 3 hours. LC-MS indicated complete de-protection at this point. The solution was concentrated to give an orange oil. The oil was dissolved in MeOH (1 mL) and HCl (1 mL, 4.0 M in dioxane) was added and the mixture was vortexed for 20 seconds. A fine suspension was observed. The mixture was concentrated to an orange powder. Ethyl ether (5 mL) was added to the powder and vortexed for 2 minutes. The solid was collected by filtration and dried under high vacuum for 16 hours to give the desired product (255) as an orange powder (0.023 g, 0.042 mmol, 31% yield, assumed 4 HCl salt). LC-MS (ESI): (exact mass: 401.23) m/e=402.2 [M+1]+. 1H NMR (400 MHz, D2O): δ 1.72 (q, 2H, J=12 Hz), 2.49 (d, 2H, J=10 Hz), 2.94 (q, 4H, J=12 Hz), 3.51–3.67 (m, 4H), 4.44 (dd, 2H, J1=12 Hz, J2=4.4 Hz), 4.57 (dd, 2H, J1=12.8 Hz, J2=3.6 Hz), 7.71 (d, 1H, J=9.2 Hz), 8.10 (dd, 1H, J1=9.2 Hz, J2=2.8 Hz), 8.44 (d, 1H, J=2.4 Hz).

Workup

  1. customcapped vial for 3 hours
  2. concentrationThe solution was concentrated
  3. customto give an orange oil
  4. concentrationThe mixture was concentrated to an orange powder
  5. additionEthyl ether (5 mL) was added to the powder
  6. waitvortexed for 2 minutes
  7. filtrationThe solid was collected by filtration
  8. customdried under high vacuum for 16 hours

Sources & evidence

ORD record
ord-3f40b13288d24493a712b6ededdbdf2a
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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