Ethanol → HCID 54557299, compound

HRID 2083779Notes

Reaction equation

HRID 2083779 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][C@@H:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@@H:9]1[OH:10])=[O:6].[N:19]([O-])=[O:20].[Na+].O.C(O)C>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:19]=[O:20])[C:5]([NH:7][C@@H:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@@H:9]1[OH:10])=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 23668193Sodium Nitrite2×HCID 54500302HCID 54500302, compound

Product 1

HCID 54557299HCID 54557299, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-(2-chloroethyl)-3-(β-D-mannopyranosyl)urea (500 mg) was dissolved in 10 ml of 99% formic acid, and the resulting solution was admixed with 250 mg of sodium nitrite in an ice-bath under stirring, while the sodium nitrite was added in small portions to said solution. The mixture was agitated for 1 hour and then admixed with 10 ml of cold water, followed by agitation for further 30 minutes to complete the nitrosation. The reaction solution was treated with 20 ml of Amberlite IR-120 (H+ form) and was then agitated for 20 minutes for the removal of sodium cation. After the cation-exchange resin was filtered off from the reaction mixture, the filtrate was concentrated to dryness by evaporating the solvent under a reduced pressure. A crystalline solid was yielded. This solid was digested with ethanol to give the titled compound. Yield 308 mg (55.9%). mp. 98°-100° C (decomposition with foaming). [α]D25 -10° (c 0.5, H2O).

Workup

  1. additionwas added in small portions
  2. waitfollowed by agitation for further 30 minutes
  3. additionThe reaction solution was treated with 20 ml of Amberlite IR-120 (H+ form)
  4. filtrationAfter the cation-exchange resin was filtered off from the reaction mixture
  5. concentrationthe filtrate was concentrated to dryness
  6. customby evaporating the solvent under a reduced pressure
  7. customA crystalline solid was yielded

Sources & evidence

ORD record
ord-fa4c4cf3b02d4aab881249ca9227828f
Source dataset
uspto-grants-1978_04
Patent number
US04086415

Reaction notes

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