Hydrochloric Acid → HCID 70099545, compound

HRID 1740731Notes

Reaction equation

HRID 1740731 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][N:15]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][CH2:19][O:18][C:17]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:16]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.CCOCC>C(O)C>[ClH:31].[Cl:31][C:29]1[CH:28]=[CH:27][C:17]2[O:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N: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:16]=2[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 57031569HCID 57031569, compound

Product 1

HCID 70099545HCID 70099545, compoundYield 135.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.77 g, 1.73 mmol) was dissolved in ethanol (7.5 ml) and 2 N sodium hydroxide (2.86 ml, 5.71 mmol) was added. The mixture was stirred at room temperature for 16 h. The ethanol was evaporated in vacuo and the remainder was diluted with water (25 ml). pH was adjusted to 6 by addition of 6 N hydrochloric acid and the aqueous solution was extracted with dichloromethane (3×15 ml). The combined organic extracts were dried over MgSO4 and evaporated in vacuo. The remainder was dissolved in tetrahydrofuran (15 ml) and 2.5 N hydrogen chloride in ether (0.59 ml, 1.47 mmol) was added dropwise. Ether (30 ml) was added and the mixture was stirred for 3 h, the precipitate was filtered off and dried, to afford 0.53 g (68%) of the title compound as a powder.

Workup

  1. customThe ethanol was evaporated in vacuo
  2. additionthe remainder was diluted with water (25 ml)
  3. additionpH was adjusted to 6 by addition of 6 N hydrochloric acid
  4. extractionthe aqueous solution was extracted with dichloromethane (3×15 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. customevaporated in vacuo
  7. dissolutionThe remainder was dissolved in tetrahydrofuran (15 ml)
  8. stirringthe mixture was stirred for 3 h
  9. filtrationthe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-c982500b2fdc4b93af3a9dc0e0ebfd52
Source dataset
uspto-grants-1999_10
Patent number
US05972925

Reaction notes

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