Sodium Hydroxide → HCID 86586636, compound

HRID 322213Notes

Reaction equation

HRID 322213 reaction equation
[C:1]([C:4]1[C:9]([CH3:10])=[C:8]([N:11]2[CH:16]=[CH:15][CH2:14][CH:13]=[CH:12]2)[CH:7]([CH2:17][O:18][CH2:19][CH2:20][N:21]=[N+:22]=[N-:23])[C:6]2(C(OCCC#N)=O)[O:24][CH2:25][O:26][C:5]=12)(=[O:3])[CH3:2].[OH-:34].[Na+].[O:36]1[CH2:41]COCC1>>[C:1]([C:4]1[C:5]2[O:26][CH2:25][O:24][C:6]=2[C:7]([CH2:17][O:18][CH2:19][CH2:20][N:21]=[N+:22]=[N-:23])=[C:8]([N:11]2[CH:12]=[CH:13][CH2:14][C:15]([C:41]([OH:36])=[O:34])=[CH:16]2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86586637HCID 86586637, compound

Product 1

HCID 86586636HCID 86586636, compoundYield 25%

Procedure

This product was obtained from deprotection of two batches of 5-acetyl-2-((2-azidoethyl)oxy)methyl-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(3,4-methylenedioxy)phenylpyridine obtained from the previous experiment (340 mg and 200 mg) and were combined after completion of the reaction. A mixture of 5-acetyl-2-((2-azidoethyl)oxy)methyl-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(3,4-methylenedioxy)phenylpyridine (340 mg, 0.750 mmol; 200 mg (60%), 0.200 mmol), 1N NaOH (1.12 mL; 0.40 mL) in a mixture of dioxane (3 mL; 3 mL) were stirred at room temperature for 1.5 hours. The two batches were concentrated in vacuo, the combined batches were dissolved in 40 mL of water, washed with dichloromethane (30 mL) and EtOAc (20 mL), acidified with 1N HCl solution (pH=4-5), and extracted with dichloromethane (2×50 mL). The combined dichloromethane extracts were washed with brine (40 mL), dried (MgSO4), and the solvent was removed in vacuo to give 300 mg (25%) of the title compound as a yellow paste which solidified on standing: mp 120° C. (decomp.). The product was used in the next step after spectral characterization.

Workup

  1. customobtained from the previous experiment (340 mg and 200 mg)
  2. customafter completion of the reaction
  3. concentrationThe two batches were concentrated in vacuo
  4. dissolutionthe combined batches were dissolved in 40 mL of water
  5. washwashed with dichloromethane (30 mL) and EtOAc (20 mL)
  6. extractionextracted with dichloromethane (2×50 mL)
  7. washThe combined dichloromethane extracts were washed with brine (40 mL)
  8. dry with materialdried (MgSO4)
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9e17dd8dda7242739943bc0fa6ce68eb
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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