Sodium Iodide → HCID 11514167, compound

HRID 2218562Notes

Reaction equation

HRID 2218562 reaction equation
[H-].[Na+].C(OC(=O)[NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[NH:16][S:17]([CH2:20][CH2:21][CH2:22][CH2:23]Cl)(=[O:19])=[O:18])(C)(C)C.[I-].[Na+]>>[O:18]=[S:17]1(=[O:19])[CH2:20][CH2:21][CH2:22][CH2:23][N:16]1[C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH2:9]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 24758Sodium hydride2×HCID 68977487HCID 68977487, compound

Product 1

HCID 11514167HCID 11514167, compound

Procedure

Sodium hydride (60% dispersion in mineral oil, 15 mg, 0.38 mmol) was added at 0° C. to a solution of trans-[2-(4-chloro-butane-1-sulfonylamino)-cyclohexyl]-carbamic acid tert-butyl ester (125 mg, 0.34 mmol) and sodium iodide (51 mg, 0.34 mmol), and the reaction mixture was stirred at room temperature for 24 h, then another portion of sodium hydride (15 mg, 0.38 mmol) was added, and the reaction mixture was heated at 60° C. for 3 h. After cooling, the solution was partitioned between heptane/ethyl acetate (1:1) and water. The organic layer was washed with brine, evaporated, and chromatographed (SiO2, heptane-ethyl acetate gradient). The title compound was obtained from this material in accordance with the general method of example 27b. Off-white solid, MS (ISP) 233.1 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated at 60° C. for 3 h
  2. temperatureAfter cooling
  3. customthe solution was partitioned between heptane/ethyl acetate (1:1) and water
  4. washThe organic layer was washed with brine
  5. customevaporated
  6. customchromatographed (SiO2, heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-950c4292cac14c1d8dd3bdbb69b97037
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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