Cyclohexylamine → HCID 22813516, compound

HRID 1733227Notes

Reaction equation

HRID 1733227 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl:20][CH2:21][CH2:22][N:23]=[C:24]=[O:25]>CO.O1CCCC1.C(O)=O>[Cl:20][CH2:21][CH2:22][NH:23][C:24]([N:19]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4])=[O:25]

Participants

7

Reactant 3

HCID 7965CyclohexylamineHCID 160352-Chloroethyl isocyanateHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 22813516HCID 22813516, compoundYield 43.7%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
60 °C

Procedure

A mixture of 3.6 g of D-galactose, 10 g of cyclohexylamine and 20 ml of methanol is heated at 60° C. for one hour under stirring. After the reaction, the reaction mixture is condensed to dryness under reduced pressure and the residue is washed with ether, whereby 5.2 g of 1-cyclohexylamino-b 1-deoxy-D-galactose are obtained as a crude product. 5.2 g of said crude product are dissolved in 50 ml of methanol, and a solution of 2.3 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 obtained is dissolved in 20 ml of formic acid. The formic acid solution is allowed to stand at room temperature for 20 minutes, and 150 ml of ether-n-hexane (3:1) are added thereto. The resultant oil is purified by silica gel chromatography (Solvent:chloroform-ethyl acetatemethanol (3:1:1)). 3.2 g of 1-(2-chloroethyl)-3-cyclohexyl-3 -(D-galactopyranosyl)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 5.2 g of 1-cyclohexylamino-b 1-deoxy-D-galactose
  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 obtained
  9. customThe resultant oil is purified by silica gel chromatography (Solvent:chloroform-ethyl acetatemethanol (3:1:1))

Sources & evidence

ORD record
ord-0ffcc08474d34c3e9f88d45f696397e1
Source dataset
uspto-grants-1980_12
Patent number
US04241052

Reaction notes

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