Hydrochloric Acid → ReN-1869 (hydrochloride)

HRID 482219Notes

Reaction equation

HRID 482219 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH:14]=[C:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].[Cl:32]CCl.Cl>C(O)C>[ClH:32].[CH:25]1[C:20]2[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[C:15](=[CH:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54420997HCID 54420997, compound

Product 1

HCID 9800975ReN-1869 (hydrochloride)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (4.4 g, 11 mmol) was dissolved in ethanol (40 ml) and 4N sodium hydroxide (8.3 ml) was added. The mixture was stirred vigorously at ambient temperature for 7 h. Dichloromethane (700 ml) was added followed by 2.5N hydrochloric acid until pH 1. The phases were separated, the organic phase dried (MgSO4) and the solvent was evaporated in vacuo. The residue was re-evaporated twice with acetone and then triturated with a mixture of acetone and diethyl ether. The solid was isolated by filtration and dried in air to give 2.2 g of the title compound as a solid.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase dried (MgSO4)
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was re-evaporated twice with acetone
  5. customtriturated with a mixture of acetone and diethyl ether
  6. customThe solid was isolated by filtration
  7. customdried in air

Sources & evidence

ORD record
ord-225b8463caae49888eeef8f4f8ee69ef
Source dataset
uspto-grants-1998_08
Patent number
US05795888

Reaction notes

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