Sodium Iodide → HCID 86718356, compound

HRID 1518751Notes

Reaction equation

HRID 1518751 reaction equation
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C@@H:8]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:9]([CH3:12])[CH2:10][OH:11].Br[CH2:23][C:24]([OH:26])=[O:25].[I-].[Na+]>C1COCC1>[C:16]([O:15][C:14]([N:13]([CH3:21])[C@H:8]([C:4]1[O:3][CH:7]=[CH:6][CH:5]=1)[C@H:9]([CH3:12])[CH2:10][O:11][CH2:23][C:24]([OH:26])=[O:25])=[O:20])([CH3:17])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 86718354HCID 86718354, compound

Product 1

HCID 86718356HCID 86718356, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (60%, 134.0 mg, 3.4 mmol, 3.0 equiv) in THF (2.2 mL) at 0° C. was added 2.6.1a (300.0 mg, 1.1 mmol), bromoacetic acid (464.0 mg, 3.4 mmol, 3.0 equiv) and sodium iodide (167.0 mg, 1.1 mmol) successively. After stirring for 7 hours at room temperature, the reaction mixture was quenched with water at 0° C., diluted with EtOAc, and acidified with aqueous 1.0 N HCl aq. solution. The organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give [(2S,3S)-3-(tert-butoxycarbonyl methylamino)-3-furan-2-yl-2-methyl-propoxy]acetic acid (287.0 mg) which was used for the next step without further purification. MS m/z (M+Na) 350.0

Workup

  1. customthe reaction mixture was quenched with water at 0° C.
  2. additiondiluted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99663b29f7c945bc92aca0a75a389fbf
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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