Hydrochloric Acid → HCID 58865792, compound

HRID 1354837Notes

Reaction equation

HRID 1354837 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]([NH:55][C:56]([C:58]4[CH:63]=[CH:62][C:61]([NH:64][C:65]([C:67]5[CH:76]=[CH:75][C:74]6[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=6)[C:68]=5[OH:77])=[O:66])=[CH:60][CH:59]=4)=[O:57])[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]([NH:55][C:56]([C:58]4[CH:63]=[CH:62][C:61]([NH:64][C:65]([C:67]5[CH:76]=[CH:75][C:74]6[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=6)[C:68]=5[OH:77])=[O:66])=[CH:60][CH:59]=4)=[O:57])[CH:29]=3)[N:24]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58865449HCID 58865449, compound

Product 1

HCID 58865792HCID 58865792, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-Hydroxy-naphthalene-2-carboxylic acid [4-(2,3-bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-quinoxalin-6-ylcarbamoyl)-phenyl]-amide (253) (9 mg, 8.5 μmmol) was dissolved in TFA (1 mL) and the mixture was shaken in a Teflon septum capped vial at room temperature 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 (254) as a yellow/green powder (5.4 mg, 6.69 μmmol, 78.7% yield, assuming a 4 HCl salt). LC-MS (ESI): (exact mass: 660.33) m/e=661.6 [M+1]+. 1H NMR (400 MHz, D2O): δ 1.70–1.82 (m, 2H), 2.61–2.65 (m, 2H), 2.78–2.94 (m, 2H), 3.57–3.60 (m, 2H), 3.67–3.68 (m, 4H), 3.97 (d, 2H, J=9.6 Hz), 4.23 (d, 2H, J=9.6 Hz), 6.89 (d, 1H, J=8.8 Hz), 7.14 (d, 1H, J=8.4 Hz), 7.18–7.29 (m, 3H), 7.32–7.53 (m, 6H), 7.74 (d, 2H, J=7.6 Hz).

Workup

  1. customcapped vial at room temperature 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-2ffc3a3fa6994f93822cfb48141c58f4
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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