Hydrochloric Acid → HCID 18924633, compound

HRID 1288677Notes

Reaction equation

HRID 1288677 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH:17][CH:18]([CH2:22][CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20]>C(OCC)(=O)C>[OH:17][CH:18]([CH2:22][CH2:23][CH2:24][CH3:25])[C:19]([O:21][CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 998242-Hydroxyhexanoic acid

Product 1

HCID 18924633HCID 18924633, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 90 ml of ethyl acetate, the 2-hydroxy-L-hexanoic acid (H-L-norLEUA-OH) was dissolved. A solution (15.1 g/30 ml) of diphenyldiazomethane in ethyl acetate was added dropwise to the resulting solution, followed by stirring overnight at room temperature. The reaction mixture was adjusted to pH 2 with 2N--HCl, followed by washing thrice with 200 ml portions of a saturated aqueous solution of sodium bicarbonate. The organic layer so obtained was dried over anhydrous magnesium sulfate and then filtered. The filtrate was thereafter concentrated under reduced pressure. The residue obtained was then purified by subjecting to chromatography on a silica gel column (toluene:ethyl acetate=20:1), whereby 11.35 g of the title compound were obtained as pale yellow crystals (yield: 54.7%).

Workup

  1. washby washing thrice with 200 ml portions of a saturated aqueous solution of sodium bicarbonate
  2. customThe organic layer so obtained
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was thereafter concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas then purified

Sources & evidence

ORD record
ord-eb5527645ad14cc09766b57ab843a012
Source dataset
uspto-grants-1998_05
Patent number
US05747448

Reaction notes

Loading…