Hydrochloric Acid → HCID 67280582, compound

HRID 1516326Notes

Reaction equation

HRID 1516326 reaction equation
[OH:1][C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([I:11])=[CH:7][CH:8]=2)[C@@H:3]1[NH:12][C:13](=[O:19])OC(C)(C)C.Cl.[OH-].[Na+].[F:23][C:24]1[CH:32]=[CH:31][C:27](C(Cl)=O)=[CH:26][CH:25]=1>O1CCOCC1>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:13]([NH:12][C@H:3]2[C:4]3[C:9](=[CH:8][CH:7]=[C:6]([I:11])[CH:5]=3)[CH2:10][C@@H:2]2[OH:1])=[O:19])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 67280700HCID 67280700, compound

Product 1

HCID 67280582HCID 67280582, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-hydroxy-6-iodo-indan-1-yl]carbamate (39.6 mmol, 14.9 g) in 1,4-dioxane (200 mL), add a solution of 4 M hydrogen chloride in dioxane (100 mL) at room temperature and stir for 2 hr. Concentrate the resulting suspension in vacuo and dry in a vacuum oven for 48 hr. Dissolve the residue in THF (25 mL) and cool in an ice bath for 30 min. Add 5 M aqueous sodium hydroxide (17.4 mL, 87.2 mmol) and 4-fluorobenzoyl chloride (3.78 mL, 40.4 mmol) dropwise. Warm the solution to room temperature and stir for one hour. Concentrate the black solution in vacuo and dilute with water (50 mL). Collect the solid by filtration and dry at 40° C. in a vacuum oven overnight to obtain the title compound (14.4 g, 91%). LC-ES/MS m/z 398 [M+H]+.

Workup

  1. concentrationConcentrate the resulting suspension in vacuo
  2. customdry in a vacuum oven for 48 hr
  3. dissolutionDissolve the residue in THF (25 mL)
  4. temperaturecool in an ice bath for 30 min
  5. stirringstir for one hour
  6. concentrationConcentrate the black solution in vacuo
  7. additiondilute with water (50 mL)
  8. customCollect the solid
  9. filtrationby filtration
  10. customdry at 40° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-6531cc9f4a8847ea99df494088f5cdc9
Source dataset
uspto-grants-2012_07
Patent number
US08227468B2

Reaction notes

Loading…