Hydrochloric Acid → HCID 21842201, compound

HRID 1737224Notes

Reaction equation

HRID 1737224 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[N:11]([CH2:13][CH2:14][CH2:15][N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][CH2:19][C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]1=2)[CH3:12])C.CO.[OH-].[Na+].Cl>O.O1CCCC1>[CH:27]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:16]([CH2:15][CH2:14][CH2:13][N:11]([C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4]([OH:31])=[O:3])[CH3:12])[C:17]=2[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 53731459HCID 53731459, compound

Product 1

HCID 21842201HCID 21842201, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of the above crude ester (6.60 g), methanol (50 ml), tetrahydrofuran (30 ml) and 4N sodium hydroxide (10 ml) was stirred at room temperature for 24 h, at 65° C. for 9 h and then at room temperature for 48 h. Water (100 ml) and concentrated hydrochloric acid (10 ml) were added and the product was extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (100 g) using a gradient of heptane and ethyl acetate (1:1→0:1). This afforded 1.93 g (50%) of the title compound as an oil, which crystallised after standing 1 day at room temperature. The product was recrystallised from a mixture of ethyl acetate and heptane to give 1.45 g of the title compound.

Workup

  1. waitat room temperature for 48 h
  2. extractionthe product was extracted with dichloromethane (3×20 ml)
  3. washThe combined organic extracts were washed with brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (100 g)
  7. customThis afforded 1.93 g (50%) of the title compound as an oil, which crystallised
  8. waitafter standing 1 day at room temperature
  9. customThe product was recrystallised from a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-7e92a291c76f4cfe8e17656b02fdb4bf
Source dataset
uspto-grants-1999_10
Patent number
US05962449

Reaction notes

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