Isopropanol → HCID 19603840, compound

HRID 2292490Notes

Reaction equation

HRID 2292490 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([CH2:15][C:16]([OH:18])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][CH:23](O)[CH3:24].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([CH2:15][C:16]([O:18][CH:23]([CH3:24])[CH3:22])=[O:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19603791HCID 19603791, compound

Product 1

HCID 19603840HCID 19603840, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-benzyloxy-2-nitrophenylacetic acid (25.1 g) in methylene chloride (250 ml) were added in turn 2-propanol (27 ml), 4-dimethylaminopyridine (1.07 and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (18.4 g) and the resulting mixture was stirred at room temperature for one hour and then allowed to stand overnight. After the solvent was distilled off under reduced pressure, the resulting residue was diluted with ethyl acetate, washed subsequently with 1N hydrochloric acid and saturated saline. The organic layer was dried over magnesium sulfate and distilled off under reduced pressure. The dark yellow oily substance thus obtained (29.7 g) was purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (22.5 g).

Workup

  1. waitto stand overnight
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed subsequently with 1N hydrochloric acid and saturated saline
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe dark yellow oily substance thus obtained (29.7 g)
  8. customwas purified by a silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2e53e0f9c9804bdea1c91b5f03f68570
Source dataset
uspto-grants-1997_11
Patent number
US05684003

Reaction notes

Loading…