Succinic Acid → HCID 131711518, compound

HRID 263361Notes

Reaction equation

HRID 263361 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:13][C@H:7]([O:8]CCCC)[C@H:6]([OH:14])[C@@H:5]([OH:15])[C@@H:4]1[OH:16].[C:17](O)(=O)[CH2:18][CH2:19][C:20](O)=O.[Cl:25][CH2:26][CH2:27][N:28]([N:40]=[O:41])[C:29](=O)[O:30]C1C=CC=CC=1C#N.C([OH:45])(C)C>CN(C)C=O.O1CCCC1.C1C=CC=CC=1>[CH2:20]([C@@:7]1([O:13][C@H:3]([CH:2]([NH:1][C:29](=[O:30])[N:28]([CH2:27][CH2:26][Cl:25])[N:40]=[O:41])[OH:45])[C@@H:4]([OH:16])[C@H:5]([OH:15])[C@H:6]1[OH:14])[OH:8])[CH2:19][CH2:18][CH3:17]

Participants

8

Reactant 4

HCID 1110Succinic AcidHCID 3776IsopropanolHCID 20234556o-cyanophenyl N-(2-chloroethyl)-N-nitrosocarbamateHCID 53681937HCID 53681937, compound

Product 1

HCID 131711518HCID 131711518, compoundYield 84.6%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.35 g (10 mmol) of n-butyl 6-amino-6-deoxy-α-D-glucopyranoside is dissolved in a mixture of 50 ml isopropanol and 50 ml dimethylformamide, and to this solution is added succinic acid powder, with stirring, to adjust the PH of the solution to 9.1. The resulting solution is then added dropwise to a solution prepared by dissolving 3.17 g (12.5 mmol) of o-cyanophenyl N-(2-chloroethyl)-N-nitrosocarbamate in a mixture of 20 ml tetrahydrofuran and 10 ml benzene, while stirring, at 0°-10° C. over 30 minutes. The resultant mixture is stirred at the same temperature for a further 2 hours, and thus reacted solution is, after filtering, concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with n-hexane and then with ethyl ether, dried under reduced pressure, and recrystallized from isopropanol to give 3.13 g of 3-(n-butyl α-D-glucopyranos-6-yl)-1-(2-chloroethyl)-1-nitrosourea. Yield 84.6%. mp 108°-109° C. (decomp.). [α]D25 +147° (C 0.5, water). Analysis for C13H24N3O7Cl (MW 369.80):

Workup

  1. additionThe resulting solution is then added dropwise to a solution
  2. customprepared
  3. stirringwhile stirring, at 0°-10° C. over 30 minutes
  4. filtrationafter filtering
  5. concentrationconcentrated at 40° C.
  6. customThe crystalline residue obtained
  7. washis washed with n-hexane
  8. dry with materialwith ethyl ether, dried under reduced pressure
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-0d9f924e81e848e7916b8c36c01ac923
Source dataset
uspto-grants-1979_05
Patent number
US04156777

Reaction notes

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