Benzylamine → HCID 53719605, compound

HRID 1733242Notes

Reaction equation

HRID 1733242 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24]>CO.O1CCCC1.C(O)=O>[Cl:19][CH2:20][CH2:21][NH:22][C:23]([N:18]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]1[O:10][CH2:2][C@H:3]([OH:4])[C@H:5]([OH:6])[C@H:7]1[OH:8])=[O:24]

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 160352-Chloroethyl isocyanateHCID 5460291aldehydo-L-arabinose

Product 1

HCID 53719605HCID 53719605, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolvent2×HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.0 g of L-arabinose, 4.3 g of benzylamine and 10 ml of methanol is heated at 60° C. for one hour under stirring. After the reaction, the mixture is condensed to dryness under reduced pressure and the residue is washed with ether, whereby 4.7 g of 1-benzylamino-1-deoxy-L-arabinose are obtained as a crude product. 4.7 g of said crude product are dissolved in 30 ml of methanol, and a solution of 2.5 g of 2-chloroethyl isocyanate in 10 ml of tetrahydrofuran is added dropwise thereto at 0° to 5° C. The solution is stirred at room temperature for one hour. Then, the reaction solution is condensed under reduced pressure, and the residue thus obtained is dissolved in 15 ml of formic acid. The formic acid solution is allowed to stand at room temperature for 15 minutes, and 150 ml of ether-n-hexane (3:1) are added thereto. The resultant oil is collected by decantation, washed with ether and then purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol (2:5:1)). 6.2 g of 1-(2-chloroethyl)-3-benzyl-3-(L-arabinopyranosyl)urea are thereby obtained as colorless caramel.

Workup

  1. customAfter the reaction
  2. customcondensed to dryness under reduced pressure
  3. washthe residue is washed with ether, whereby 4.7 g of 1-benzylamino-1-deoxy-L-arabinose
  4. customare obtained as a crude product
  5. customat 0° to 5° C
  6. stirringThe solution is stirred at room temperature for one hour
  7. customcondensed under reduced pressure
  8. customthe residue thus obtained
  9. customThe resultant oil is collected by decantation
  10. washwashed with ether
  11. custompurified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol (2:5:1))

Sources & evidence

ORD record
ord-a18379bdd63144da9d2f6186cf15d958
Source dataset
uspto-grants-1980_12
Patent number
US04241052

Reaction notes

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