Hydrochloric Acid → HCID 70435269, compound

HRID 653101Notes

Reaction equation

HRID 653101 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.[ClH:21].C[O:23][C:24](=[O:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][NH:26]1.C(N(CC)CC)C.Cl>C(OCC)C.O.C1(C)C=CC=CC=1>[OH2:10].[ClH:21].[N+:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][N:26]3[CH2:27][CH2:28][CH2:29][C@H:25]3[C:24]([OH:30])=[O:23])=[CH:20][C:7]=2[C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2733200methyl L-prolinate hydrochlorideHCID 13531604HCID 13531604, compound

Product 1

HCID 70435269HCID 70435269, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2 g. (0.006 mole) of 5-bromomethyl-2-nitro-3-phenylbenzofuran, 0.9 g. (0.006 mole) of L-proline methylesterhydrochloride (available from the Aldrich Chemical Company) and 1.2 g. (0.012 mole) of triethylamine in 100 ml. of toluene is heated at reflux for about 100 hours. The mixture is extracted three times with 50 ml. portions of water. The organic layer is then extracted repeatedly with 50 ml. portions of 3N hydrochloric acid to remove all of the yellow product from the toluene layer. The aqueous layer is neutralized with 10 percent sodium carbonate solution. The aqueous layer is then extracted with dichloromethane until the water is colorless. The dichloromethane layer is dried, then evaporated to provide a residue which is diluted with diethyl ether to provide a brownish precipitate. The solid is removed by filtration, and the filtrate is concentrated to provide a residue. The residue is suspended in 50 ml. of concentrated hydrochloric acid diluted 1:1 with water. The mixture is heated at 90° C. for three hours. The mixture is cooled and filtered to provide a yellow precipitate. The precipitate is washed with water to provide N-[(2-nitro-3-phenylbenzofuran-5-yl)methyl]-L-proline hydrochloride hydrate, m.p. 109°-110° C., having the structure

Workup

  1. additionA mixture of 2 g
  2. temperatureat reflux for about 100 hours
  3. extractionThe mixture is extracted three times with 50 ml
  4. extractionThe organic layer is then extracted repeatedly with 50 ml
  5. customportions of 3N hydrochloric acid to remove all of the yellow product from the toluene layer
  6. extractionThe aqueous layer is then extracted with dichloromethane until the water
  7. dry with materialThe dichloromethane layer is dried
  8. customevaporated
  9. customto provide a residue which
  10. customto provide a brownish precipitate
  11. customThe solid is removed by filtration
  12. concentrationthe filtrate is concentrated
  13. customto provide a residue
  14. temperatureThe mixture is cooled
  15. filtrationfiltered
  16. customto provide a yellow precipitate
  17. washThe precipitate is washed with water

Sources & evidence

ORD record
ord-fd5ed60d05b6406584f8f5a58e8e890c
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

Loading…