Sodium Sulfite → HCID 71127330, compound

HRID 1912076Notes

Reaction equation

HRID 1912076 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:21](=[N:33][O:34]C)[C:22]#[C:23][CH:24]1[CH2:27][CH:26]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25]1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:36]Cl.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:21]1[C:22]([I:36])=[C:23]([CH:24]2[CH2:27][CH:26]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25]2)[O:34][N:33]=1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 24640Iodine chlorideHCID 86675044tert-Butyl 3-(3-benzyloxypropyl)-6-[3-(2,2-dimethylpropyl)cyclobutyl]-4-methoxyimino-5-hexynoate

Product 1

HCID 71127330HCID 71127330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(3-benzyloxypropyl)-6-[3-(2,2-dimethylpropyl)cyclobutyl]-4-methoxyimino-5-hexynoate (3.37 g) and methylene chloride (70 mL) were mixed. To the mixture was added iodine monochloride (1 M in methylene chloride) (7.66 mL) at ice temperature. The mixture was stirred at ice temperature for 1 hr, and then to the mixture was added aqueous solution of sodium sulfite. The mixture was extracted with chloroform. The organic layer was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (4.21 g) as a crude product.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-31367f32e21449c5bb87bc5353003ff5
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

Loading…