Hydrochloric Acid → HCID 45264600, compound

HRID 2226747Notes

Reaction equation

HRID 2226747 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]=[C:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][CH2:21][C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:36]CCl>C(O)C>[ClH:36].[CH:29]1[C:20]2[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:18](=[CH:17][CH2:16][O:15][CH2:14][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:19]=2[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 11070095HCID 11070095, compound

Product 1

HCID 45264600HCID 45264600, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (2.5 g, 5.8 mmol) was dissolved in ethanol (15 ml) and a 4 N sodium hydroxide solution (4.3 ml) was added. The mixture was stirred vigorously at room temperature for 5 h. A 4 N hydrochloric acid solution was added until pH 1 followed by dichloromethane (400 ml). The mixture was stirred vigorously for a few minutes and the phases were separated. The organic phase was dried over sodium sulphate and the solvent was evaporated in vacuo. The residue was evaporated twice with acetone, once with ethyl acetate, dissolved in acetone (15 ml) and left for crystallization. This afforded 1.9 g of the title compound as a solid.

Workup

  1. stirringThe mixture was stirred vigorously for a few minutes
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was evaporated twice with acetone, once with ethyl acetate
  6. dissolutiondissolved in acetone (15 ml)
  7. waitleft for crystallization

Sources & evidence

ORD record
ord-b51fc00bbcb8484f9212a219331f0828
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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