Acetic Acid → HCID 18387472, compound

HRID 2296614Notes

Reaction equation

HRID 2296614 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH:5]([NH:8][CH2:9][CH2:10][OH:11])([CH3:7])[CH3:6].[F:12][C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[CH:15]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH2:38]>C1COCC1>[C:1]([OH:4])(=[O:3])[C:2]([OH:11])=[O:38].[F:12][C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[CH2:15][N:8]([CH:5]([CH3:7])[CH3:6])[CH2:9][CH2:10][OH:11]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 79942-(Isopropylamino)ethanolHCID 27347702-Fluoro-5-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18387472HCID 18387472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To acetic acid (25.76 ml, 450 mmol) and 2-(isopropylamino)ethanol (51.76 ml, 450 mmol) in dry THF (750 ml) at 0° C. was added 2-fluoro-5-nitrobenzaldehyde (75.88 g, 450 mmol) and sodium triacetoxyborohydride (141.99 g, 670 mmol) portionwise. The reaction was allowed to warm to room temperature and was stirred for 3 h. The mixture was taken up in acidic water and washed with methylene chloride (250 ml), made basic with 50% sodium hydroxide (150 ml) and extracted with methylene chloride (3×250 ml). The extracts were dried with magnesium sulfate, filtered, and concentrated to an oil. The oil was dissolved in 95% ethanol and treated with isopropanol-oxalic acid. The oxalate salt was collected by filtration (31.2 g, 20%), m.p. 106-107° C.

Workup

  1. washwashed with methylene chloride (250 ml)
  2. extractionextracted with methylene chloride (3×250 ml)
  3. dry with materialThe extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. dissolutionThe oil was dissolved in 95% ethanol
  7. additiontreated with isopropanol-oxalic acid
  8. filtrationThe oxalate salt was collected by filtration (31.2 g, 20%), m.p. 106-107° C.

Sources & evidence

ORD record
ord-43dc2686b22a49bd85a12825405d1687
Source dataset
uspto-grants-2002_12
Patent number
US06489322B1

Reaction notes

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