Ethanol → HCID 54402306, compound

HRID 1460440Notes

Reaction equation

HRID 1460440 reaction equation
O.N[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6].[K+].[Br-:12].N([O-])=O.[Na+].CCO>OS(O)(=O)=O.O>[Br:12][C@@H:3]([CH2:4][C:5](=[O:7])[NH2:6])[C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 702EthanolHCID 170358L-Asparagine, monohydrateHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

Product 1

HCID 54402306HCID 54402306, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

L-Asparagine monohydrate 1* (37.5 g, 0.25 mol) was dissolved in 3M H2SO4 (330 ml) and treated with KBr (39.3 g, 0.75 mol). The solution was stirred and cooled in an ice-MeOH bath to ca. -10° C. Some precipitation occurred. A solution of NaNO2 (21.6 g, 0.31 mol) in H2O (38 ml) was added dropwise over 80 minutes. The internal temperature was kept at -10° to -5° during the addition and for 90 minutes afterward. The mixture was filtered and the solid portion washed with ice cold H2O (3x) and dried overnight to give the product 2* (31.64 g, 65%) as an off-white solid: [α]D =-67.8° (C 4.51, EtOH). ##STR93##

Workup

  1. customSome precipitation
  2. additionThe internal temperature was kept at -10° to -5° during the addition and for 90 minutes afterward
  3. filtrationThe mixture was filtered
  4. washthe solid portion washed with ice cold H2O (3x)
  5. customdried overnight
  6. customto give the product 2* (31.64 g, 65%) as an off-white solid

Sources & evidence

ORD record
ord-70b173322b3f486ba457c62240e5983d
Source dataset
uspto-grants-1991_12
Patent number
US05071843

Reaction notes

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