Sodium Iodide → HCID 68283670, compound

HRID 1527429Notes

Reaction equation

HRID 1527429 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][C@:11]2([CH2:17]OS(C)(=O)=O)[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[I-].CO[CH2:27][CH2:28]OC>[Zn]>[CH2:27]([O:16][C:14]([C@@H:13]1[CH2:12][C@:11]2([CH3:17])[C@@H:9]([CH2:10]2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:15])[CH3:28]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80711,2-DimethoxyethaneHCID 86673856HCID 86673856, compound

Product 1

HCID 68283670HCID 68283670, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a solution of (1R,3S,5S)-5-methanesulfonyloxymethyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (100 mg, 0.24 mmol) in DME (2.6 mL) were successively added NaI (355 mg, 2.37 mmol) and zinc powder (155 mg, 2.37 mmol). The reaction mixture was refluxed 30 min under argon atmosphere, cooled to RT and quenched by addition of a saturated aqueous solution of NH4Cl (1.6 mL). CH2Cl2 (1.6 mL) and few Na2S crystals were added and the biphasic mixture was stirred at RT for 1 h. The layers were separated, the organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (eluent: c-hexane to c-hexane/EtOAc). TLC, Rf (c-hexane/EtOAc 2:1)=0.60; MS (UPLC/MS): 270.3 [M+H]+, 214.2 [MH−tBu]+, 170.2 [MH−Boc]+; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 4.11 (m, 2H), 3.95 (m, 1H), 3.10 (m, 1H), 2.42 (m, 1H), 1.84 (m, 1H), 1.38 (m, 9H), 1.20 (t, 3H), 1.18 (s, 3H) 0.69 (dd, 1H), 0.64 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed 30 min under argon atmosphere
  2. customquenched by addition of a saturated aqueous solution of NH4Cl (1.6 mL)
  3. additionCH2Cl2 (1.6 mL) and few Na2S crystals were added
  4. customThe layers were separated
  5. washthe organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by flash column chromatography on silica gel (eluent: c-hexane to c-hexane/EtOAc)

Sources & evidence

ORD record
ord-0d9430caab7b4ccab155ecebec3737a3
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…