Hydrochloric Acid → HCID 9891037, compound

HRID 1721371Notes

Reaction equation

HRID 1721371 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[C:6]([CH3:19])=[C:5]2[CH:20]([CH3:26])[C:21]([O:23]CC)=[O:22].C1COCC1.[OH-].[Na+].Cl>O.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=1)[C:6]([CH3:19])=[C:5]2[CH:20]([CH3:26])[C:21]([OH:23])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22414953HCID 22414953, compound

Product 1

HCID 9891037HCID 9891037, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product of Step 3 (11.59 g, 24.2 mmol), THF (125 mL), MeOH (60 mL), H2O (30 mL) and 10 N NaOH (10 mL) was stirred at r.t. overnight. The mixture was then acidified with 2N HCl and the product was extracted in EtOAc, the extracts were dried over Na2SO4, and the product was purified by flash chromatography on silica with EtOAc:toluene:AcOH 5:95: 1. It was then swished in ether:hexane 1:2 to yield 10.29 g, 94%, of the title product. 1H NMR (CD3COCD3) 1.50 (3H, d), 2.38 (3H, s), 4.05 (1H, q), 5.44 (2H, s), 6.95 (2H, d), 7.16 (1H, dd), 9.28 (1H, d), 7.47 (2H, d), 7.80 (1H d).

Workup

  1. extractionthe product was extracted in EtOAc
  2. dry with materialthe extracts were dried over Na2SO4
  3. customthe product was purified by flash chromatography on silica with EtOAc:toluene:AcOH 5:95: 1
  4. customto yield 10.29 g, 94%

Sources & evidence

ORD record
ord-1281767162424cbe8d65d487f5f6a560
Source dataset
uspto-grants-1996_04
Patent number
US05510368

Reaction notes

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