Acetic Acid → HCID 53749786, compound

HRID 850628Notes

Reaction equation

HRID 850628 reaction equation
C(OC(=O)N(CCCC1C=CC=C(Br)N=1)CC=O)(C)(C)C.[C:22]([O:26][C:27](=[O:40])[CH2:28][C@H:29](N)[C:30]1[CH:31]=[N:32][CH:33]=[C:34]([O:36][CH2:37][CH3:38])[CH:35]=1)([CH3:25])([CH3:24])[CH3:23].C(O)(=O)C.CC([O-])=O.[Na+].[BH3-]C#N.[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>CC(O)C.C(OCC)(=O)C>[C:22]([O:26][C:27](=[O:40])[CH2:28][CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34]([O:36][CH2:37][CH3:38])[CH:35]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

10

Reactant 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 54274193HCID 54274193, compoundHCID 54504767HCID 54504767, compound

Product 1

HCID 53749786HCID 53749786, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the crude aldehyde 20-8 (0.671 g,.1.88 mmol), amine 15-8 (0.651 g, 2.44 mmol), acetic acid (0.107 mL, 1.88 mmol), NaOAc (1.54 g, 18.8 mmol), and powdered molecular sieves (1.20 g) in 2-propanol (15 mL) was stirred for 20 minutes. The mixture was cooled to 0° C. and then NaBH3CN (0.354 g, 5.64 mmol) was added. After stirring 6 hours, the pH of the mixture was adjusted to ~2 with 1N HCl. The solution was stirred for an additional 10 minutes, ethyl acetate (20 mL) was added, and the pH was adjusted to ~11 with 10% potassium carbonate. The organics were extracted with ethyl acetate, dried over Na2SO4, and removed in vacuo. The residue was chromatographed (silica gel, [70:25:5 CHCl3 /EtOAc/MeOH]) to give 20-9 as a yellow oil in 95% yield.

Workup

  1. stirringAfter stirring 6 hours
  2. stirringThe solution was stirred for an additional 10 minutes
  3. extractionThe organics were extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customremoved in vacuo
  6. customThe residue was chromatographed (silica gel, [70:25:5 CHCl3 /EtOAc/MeOH])

Sources & evidence

ORD record
ord-0832d5f03c6d40a58089175b56507e40
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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