Hydrochloric Acid → HCID 54002154, compound

HRID 1415883Notes

Reaction equation

HRID 1415883 reaction equation
[Br:1]Br.[CH2:3]([C@@:7]1([CH2:26][CH3:27])[NH:13][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:10]=2[S:9][CH2:8]1)[CH2:4][CH2:5][CH3:6].Cl>C(O)(=O)C>[Br:1][C:21]1[C:22]([O:24][CH3:25])=[CH:23][C:10]2[S:9][CH2:8][C@:7]([CH2:3][CH2:4][CH2:5][CH3:6])([CH2:26][CH3:27])[NH:13][C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]=2[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24408BromineHCID 53780169HCID 53780169, compound

Product 1

HCID 54002154HCID 54002154, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (18.6 g) was added to a solution of the product (10.4 g) from step (f) dissolved in glacial acetic acid (150 ml). The reaction mixture was stirred at room temperature for 2 hours. Acetic acid was removed in vacuo, added another 100 ml and concentrated in vacuo. The resulting residue was dissolved in EtOAc and washed with sodium metabisulfite and 1N NaOH. The organic layer was separated, dried and concentrated in vacuo to give a brown oil which was then converted to the hydrochloride salt with ethereal HCl. This solid was filtered, washed with ether and then treated with 1N NaOH and EtOAc to get the title product (8.9 g) as an orange oil. 1H NMR consistent with the proposed structure.

Workup

  1. customAcetic acid was removed in vacuo
  2. additionadded another 100 ml
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in EtOAc
  5. washwashed with sodium metabisulfite and 1N NaOH
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto give a brown oil which
  10. filtrationThis solid was filtered
  11. washwashed with ether
  12. additiontreated with 1N NaOH and EtOAc

Sources & evidence

ORD record
ord-1bb9aa9f00d54eb69ec6f426ce86969f
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

Loading…