Ethanol hydrochloride → HCID 86625849, compound

HRID 644145Notes

Reaction equation

HRID 644145 reaction equation
[NH2:1][C:2](=[N:32][O:33][C:34](=[O:48])[C@@H:35]([NH:40]C(OC(C)(C)C)=O)[C@@H:36]([CH3:39])[CH2:37][CH3:38])[C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.Cl.C(O)C>C(O)C>[NH2:1][C:2](=[N:32][O:33][C:34](=[O:48])[C@@H:35]([NH2:40])[C@@H:36]([CH3:39])[CH2:37][CH3:38])[C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([NH2:27])=[O:26])=[CH:28][CH:29]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochloride3×HCID 86625847HCID 86625847, compound

Product 1

HCID 86625849HCID 86625849, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (5 mL) solution of 0.20 g of 4-(3-{4-[3-(4-{amino[(2S,3S)-2-(tert-butoxycarbonyl)amino-3-methylpentanoyloxyimino]methyl}phenoxy)propyl]-1-piperidinyl}propoxy)benzamide=O-[(2S,3S)-2 (tert-butoxycarbonyl)amino-3-methylpentanoyl]oxime was added 2 mL of 2.9 mol/L hydrogen chloride/ethanol at room temperature, which was then stirred at the same temperature for 5 hours. Thereto was added 2 mL of 2.9 mol/L hydrogen chloride/ethanol, which was then stirred for 26 hours. Thereto was further added 1 mL of 2.9 mol/L hydrogen chloride/ethanol, which was then stirred for 3 days. The solvent was distilled off under reduced pressure, and the resultant solid was suspended in diisopropyl ether, followed by collecting the solid matter by filtration before washing with diisopropyl ether to provide 0.13 g of 4-{3-[4-(3-{4-[amino((2S,3S)-2-amino-3-methylpentanoyloxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-((2S,3S)-2-amino-3-methylpentanoyl)oxime hydrochloride as white solid form.

Workup

  1. stirringwas then stirred for 26 hours
  2. stirringwas then stirred for 3 days
  3. distillationThe solvent was distilled off under reduced pressure
  4. customby collecting the solid matter
  5. filtrationby filtration
  6. washbefore washing with diisopropyl ether

Sources & evidence

ORD record
ord-d88ad4b901524b7689613579682aa234
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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