Hydrochloric Acid → ReN-1869 (hydrochloride)

HRID 863550Notes

Reaction equation

HRID 863550 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-9e8b84d8492d4952875c5b1cf29c2541
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

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