Hydrochloric Acid → HCID 69947914, compound

HRID 1276404Notes

Reaction equation

HRID 1276404 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:12][CH2:13][CH2:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][CH2:18][C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]1=2)=[O:5])C.[OH-].[Na+].[ClH:32]>C(O)C.O>[ClH:32].[CH:26]1[C:17]2[CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:15]([CH2:14][CH2:13][CH2:12][N:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]3[C:4]([OH:5])=[O:3])[C:16]=2[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54010195HCID 54010195, compound

Product 1

HCID 69947914HCID 69947914, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

The above ester (0.83 g, 0.002 mol) was dissolved in a mixture of ethanol (8 ml), water (2 ml) and sodium hydroxide (0.58 g, 0.015 mol). The reaction mixture was stirred at room temperature for 50 h and at 50° C. for 5 h. Water. (50 ml) and concentrated hydrochloric acid (3 ml) were added, and the resulting mixture was extracted with dichloromethane (3×10 ml). The combined organic extracts were washed with brine (2×20 ml), dried (MgSO4) and concentrated in vacuo. The residue was re-dissolved in methanol (2 ml) and ethyl acetate (5 ml) and concentrated in vacuo. The solid residue was washed with a small amount of ethyl acetate and dried, affording 0.6 g (73%) of the title compound as a powder.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (3×10 ml)
  2. washThe combined organic extracts were washed with brine (2×20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was re-dissolved in methanol (2 ml)
  6. concentrationethyl acetate (5 ml) and concentrated in vacuo
  7. washThe solid residue was washed with a small amount of ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-ad010c08428848588687e8246cc513a0
Source dataset
uspto-grants-2000_12
Patent number
US06166009

Reaction notes

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