Norleucine, D-(-)- → Hexanoic acid, 2-hydroxy-, (2R)-

HRID 890681Notes

Reaction equation

HRID 890681 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].N([O-])=[O:11].[Na+]>S(=O)(=O)(O)O.O>[OH:11][C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 456468Norleucine, D-(-)-HCID 23668193Sodium Nitrite

Product 1

HCID 6995511Hexanoic acid, 2-hydroxy-, (2R)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of D-norleucine (500 mg, 3.81 mmol) in 10 mL of 1N aqueous sulfuric acid was added sodium nitrite (421 mg, 6.10 mmol) in 3 mL of water dropwise over a 20-minute period. The reaction mixture was allowed to slowly warm to room temperature over a 16-hour period. The mixture then was extracted with EtOAc (2×25 mL), dried (Na2SO4), and concentrated to yield 200 mg (40%) of a white waxy solid.

Workup

  1. temperatureto slowly warm to room temperature over a 16-hour period
  2. extractionThe mixture then was extracted with EtOAc (2×25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto yield 200 mg (40%) of a white waxy solid

Sources & evidence

ORD record
ord-179b506ce4f74a2ca29ba9e4692847d9
Source dataset
uspto-grants-2006_02
Patent number
US06998416B2

Reaction notes

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