Hydrochloric Acid → HCID 69584176, compound

HRID 2227779Notes

Reaction equation

HRID 2227779 reaction equation
[ClH:1].[OH:2][C@@H:3]([CH2:19][N:20]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:27][CH:26]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C(O)C.C1COCC1>[ClH:1].[OH:2][C@@H:3]([CH2:19][N:20]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:29][CH:30]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69584186HCID 69584186, compound

Product 1

HCID 69584176HCID 69584176, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of the free base (0.25 g, 0.47 mmol) from example 93 in ethanol/THF (50 mL/50 mL) was treated with 1N NaOH (14.1 mL, 14.1 mmol) and refluxed with stirring for 1 h, the reaction was neutralized with 1N HCl (13.6 mL, 13.6 mmol, 29 eq), and concentrated in vacuo. The resulting residue was slurried in ether (30 ml) and anhydrous HCl in ether (30 ml) was added. The resulting slurry was concentrated in vacuo. The residue was dissolved in EtOAc and filtered. The filtrate was concentrated in vacuo to provide 0.08 g (35%) of a tan solid. MS (FD+): m/z 463. Anal Calcd for C27H31N20O5Cl: C, 64.99; H, 6.26; N, 5.61. Found: C, 65.29; H, 6.55; N, 5.35.

Workup

  1. temperaturerefluxed
  2. concentrationconcentrated in vacuo
  3. additionanhydrous HCl in ether (30 ml) was added
  4. concentrationThe resulting slurry was concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-77f11a91db22485f87bd300d91a354a7
Source dataset
uspto-grants-2002_07
Patent number
US06413991B1

Reaction notes

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