Sodium Iodide → HCID 86721089, compound

To a solution of Intermediate 9C (61 mg, 0.213 mmol) in DCM (5 mL) was added DIEA (0.080 mL, 0.458 mmol) followed by the addition of MeSO2Cl (0.030 mL, 0.385 mmol). The reaction mixture was then stirred at rt for 0.5 h. After 30 min., the reaction mixture was concentrated. The residue was dissolved in EtOAc and washed with aqueous NaHCO3 solution followed by brine. The organic layers were then dried over MgSO4 and concentrated in vacuo to yield a clear oily residue, which was subjected to the next step without further purification. To a solution of 3-((tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)propyl methanesulfonate in acetone (5 mL) was added sodium iodide (128 mg, 0.854 mmol). The yellow suspension was refluxed for ˜4 h, and then stirred at rt for overnight. The reaction mixture was then concentrated followed by addition of small amount of water and DCM. The aqueous layer was then re-extracted with DCM (2×). The combined organic layers were concentrated and then purified by chromatography to give tert-butyl (1-(3-chlorophenyl)-3-iodopropyl)carbamate (68 mg, 81%) as yellow oil which solidified upon standing. MS (ESI) m/z: 395.9 (M+H)+.

1. waitAfter 30 min.
2. concentrationthe reaction mixture was concentrated
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with aqueous NaHCO3 solution
5. dry with materialThe organic layers were then dried over MgSO4
6. concentrationconcentrated in vacuo
7. customto yield a clear oily residue, which
8. customwas subjected to the next step without further purification
9. temperatureThe yellow suspension was refluxed for ˜4 h
10. stirringstirred at rt for overnight
11. concentrationThe reaction mixture was then concentrated
12. additionfollowed by addition of small amount of water and DCM
13. extractionThe aqueous layer was then re-extracted with DCM (2×)
14. concentrationThe combined organic layers were concentrated
15. custompurified by chromatography

ORD record

ord-cb3ec6d6dba64b878a0c8e775a3a415f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901115B2