Ethanolamine → HCID 86754029, compound

HRID 635163Notes

Reaction equation

HRID 635163 reaction equation
C(N([CH2:6][CH3:7])CC)C.[O:8]=[CH:9][C@H:10]([C@@H:12]([C@@H:14]([C@H:16]([CH3:18])[OH:17])[OH:15])[OH:13])[OH:11].[CH:19](N)([CH3:21])[CH3:20].C(CN)O.C[N:28]([CH:30]=[O:31])C>>[O:8]=[CH:9][C@H:10]([C@@H:12]([C@@H:14]([C@H:16]([CH3:18])[OH:17])[OH:15])[OH:13])[OH:11].[CH:19]([C:6](=[CH2:7])[C:30]([NH2:28])=[O:31])([CH3:21])[CH3:20]

Participants

6

Reactant 5

HCID 700EthanolamineHCID 6228Dimethylformamide3×HCID 6363IsopropylamineHCID 8471TriethylamineHCID 3034656L-(-)-Fucose

Product 1

HCID 86754029HCID 86754029, compoundYield 82%

Procedure

To a solution of pNAS (1.0 g, 5.91 mmol) in 50 mL DMF was added triethylamine (1.0 mL), followed by the dropwise addition of the L-fucose derivative 22 (356 mg, 1.18 mmol, 20 mol % with respect to pNAS). The solution was stirred at room temperature for 16 h, and subsequently heated to 40° C. for 18 h. The solution was cooled and isopropylamine (233 mg, 25 mol % with respect to pNAS) was added as a solution in DMF (1 mL). The solution was stirred at 40° C. for a further 24 h, followed by the addition of ethanolamine (2 mL, excess as a solution in 5 mL of DMF). The clear solution was stirred at room temperature for 12 h, followed by dialysis against water using dialysis tubing with a cut-off of 12,000-14,000 kD. The product was recovered by lyophilization. Yield 82%.

Workup

  1. temperaturesubsequently heated to 40° C. for 18 h
  2. temperatureThe solution was cooled
  3. stirringThe solution was stirred at 40° C. for a further 24 h
  4. stirringThe clear solution was stirred at room temperature for 12 h
  5. customfollowed by dialysis against water using dialysis tubing with a cut-off of 12,000-14,000 kD
  6. customThe product was recovered by lyophilization

Sources & evidence

ORD record
ord-3ca96057b4c4417f87fd1ff9985ab6d5
Source dataset
uspto-grants-2001_02
Patent number
US06187762B1

Reaction notes

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