Isoamylamine → HCID 58677374, compound

HRID 747559Notes

Reaction equation

HRID 747559 reaction equation
[CH:1]([C:3]1[O:7][C:6]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=O.[CH2:18]([NH2:23])[CH2:19][CH:20]([CH3:22])[CH3:21].[BH4-].[Na+]>CO>[CH3:21][CH:20]([CH3:22])[CH2:19][CH2:18][NH:23][CH2:1][C:3]1[O:7][C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH2:15])=[O:14])=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 58677377HCID 58677377, compound

Product 1

HCID 58677374HCID 58677374, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(5-Formyl-furan-2-yloxy)-benzamide (0.18 g, 0.78 mmol), isoamylamine (0.10 g, 0.1.17 mmol), 3 Å molecular sieves (2 g) in methanol (30 mL), agitate 18 hours at ambient temperature. Add sodium borohydride (0.058 g, 1.52 mmol), agitate 20 hours at ambient temperature. Filter through Celite, then concentrate in vacuo. Partition the residue between water (50 mL), and ethyl acetate (150 mL). Drain the organic layer, and dry over sodium sulfate. Purify via ISCO™ 100 c (40 g silica) using a gradient of 95:5:0.5 to 90:10:1 chloroform/ethanol/ammonium hydroxide to afford the title compound (0.160 g, 68%): mass spectrum (ion spray): m/z=303.18 (M+1); HPLC retention time: 5.79 min (HPLC method in this experiment: 5:95-95:5 ACN/0.1% TFA in water over 10 minutes using a 15 cm Zorbax column, running at 1 mL/minute, ultraviolet detector set at 254 nM).

Workup

  1. filtrationFilter through Celite
  2. concentrationconcentrate in vacuo
  3. customPartition the residue between water (50 mL), and ethyl acetate (150 mL)
  4. dry with materialdry over sodium sulfate
  5. customPurify via ISCO™ 100 c (40 g silica)

Sources & evidence

ORD record
ord-5ee4f213ec844a49abc5b72449d7fd3f
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

Loading…