Boron tribromide → HCID 18973644, compound

HRID 2394470Notes

Reaction equation

HRID 2394470 reaction equation
[CH2:1]([C:3]1[C:4](=[O:30])[N:5]([C:9]([NH:11][CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:27]CC)=[C:20]([S:23](=[O:26])(=[O:25])[NH2:24])[CH:21]=3)[O:16][CH2:15][CH2:14]2)=[O:10])[CH2:6][C:7]=1[CH3:8])[CH3:2].B(Br)(Br)Br.C(C1C(=O)N(C(NCC2C3C(=CC(OC)=C(S(=O)(=O)N)C=3)OCC2)=O)CC=1C)C>C(Cl)Cl>[CH2:1]([C:3]1[C:4](=[O:30])[N:5]([C:9]([NH:11][CH2:12][CH:13]2[C:22]3[C:17](=[CH:18][C:19]([OH:27])=[C:20]([S:23](=[O:25])(=[O:26])[NH2:24])[CH:21]=3)[O:16][CH2:15][CH2:14]2)=[O:10])[CH2:6][C:7]=1[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 18973614HCID 18973614, compoundHCID 18973664HCID 18973664, compound

Product 1

HCID 18973644HCID 18973644, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Preparation of the starting compound 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-ethoxychroman ##STR54## 9.5 ml (0.1 mol) of boron tribromide are added dropwise to a solution of 10.6 g (0.025 mol of 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-methoxychroman in 75 ml of methylene chloride cooled to -10° C. After standing overnight at 20° C., the excess boron tribromide is destroyed after cooling to -10° C. by cautious dropwise addition of methanol. The mixture is then introduced into ice/water and extracted several times with methylene chloride. The combined methylene chloride extracts are dried, evaporated and recrystallized from methanol. 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-hydroxychroman of melting point 175° C. is obtained.

Workup

  1. customthe excess boron tribromide is destroyed
  2. temperatureafter cooling to -10° C. by cautious dropwise addition of methanol
  3. additionThe mixture is then introduced into ice/water
  4. extractionextracted several times with methylene chloride
  5. dry with materialThe combined methylene chloride extracts are dried
  6. customevaporated
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e4a52410461f4b008f8a4b3b699fc51c
Source dataset
uspto-grants-1998_09
Patent number
US05811448

Reaction notes

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