Butylamine → HCID 15098509, compound

HRID 564890Notes

Reaction equation

HRID 564890 reaction equation
C1(=O)[N:5]([C@@H:6]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[O:12][C@H:7]2[O:8][CH2:9][CH:10]=[CH2:11])[C:4](=[O:19])[C:3]2=CC=CC=C12.C(N)CCC>CO>[C:4]([NH:5][C@@H:6]1[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[O:12][C@H:7]1[O:8][CH2:9][CH:10]=[CH2:11])(=[O:19])[CH3:3]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 15098529HCID 15098529, compound

Product 1

HCID 15098509HCID 15098509, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of allyl 2,3-dideoxy-2-phthalimido-β-D-glucopyranoside, Compound 22, (100 mg, 0.30 mmol) and BuNH2 (4 mL) in MeOH (20 mL) was refluxed for 10 hours, then cooled and evaporated. Acetic anhydride (2 mL) was added to a solution of the residue in MeOH (10 mL) at 0-5° C., and the mixture was stirred for three hours at 0-5° C. The mixture was concentrated, and the residue was triturated in MeOH with Et2O to give Compound 1i (40 mg, 54 percent).

Workup

  1. temperaturewas refluxed for 10 hours
  2. temperaturecooled
  3. customevaporated
  4. additionAcetic anhydride (2 mL) was added to a solution of the residue in MeOH (10 mL) at 0-5° C.
  5. concentrationThe mixture was concentrated
  6. customthe residue was triturated in MeOH with Et2O

Sources & evidence

ORD record
ord-db4e37fc8c3848ecba6ca40fdc0e5c09
Source dataset
uspto-grants-2001_01
Patent number
US06168934A

Reaction notes

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