Hydrochloric Acid → HCID 85657726, compound

HRID 654472Notes

Reaction equation

HRID 654472 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH:18]=[N:19][OH:20])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CCO>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][NH:19][OH:20])[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 85657722HCID 85657722, compound

Product 1

HCID 85657726HCID 85657726, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the oxime from Step 3 (400 mg, 1.52 mmole) in EtOH (7 mL) at 0° C. there was added pyridine-borane complex (288.5 mg, 3.10 mmole) and 4M ethanolic HCl (1.16 mL, 4.65 mmol). The mixture was stirred at 0° C. for 20 minutes, then allowed to warm up to r.t. Most of the EtOH was evaporated away, H2O (20 mL) and 1N aqueous HCl (10 mL) was added, and the mixture was extracted twice with Et2O. The aqueous fraction was then made basic with 2.5N aqueous NaOH, and extracted twice with Et2O. From these extracts a crude product was obtained which was purified by chromatography on silica gel, eluting with 5% EtOH in CH2Cl2 to afford the title product as a colorless oil.

Workup

  1. temperatureto warm up to r.t
  2. customMost of the EtOH was evaporated away
  3. additionH2O (20 mL) and 1N aqueous HCl (10 mL) was added
  4. extractionthe mixture was extracted twice with Et2O
  5. extractionextracted twice with Et2O
  6. customFrom these extracts a crude product was obtained which
  7. customwas purified by chromatography on silica gel
  8. washeluting with 5% EtOH in CH2Cl2

Sources & evidence

ORD record
ord-af0f6f3f4d7545b2b4004cb121baf09b
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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