Trimethylsilyl iodide → HCID 178525614, compound

HRID 1613499Notes

Reaction equation

HRID 1613499 reaction equation
[C:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C:13]2([CH2:18][CH:19]([CH2:23][O:24][CH2:25][CH2:26][O:27]C)[C:20]([OH:22])=[O:21])[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1)([OH:3])=[O:2].C[Si](I)(C)C>ClCCl>[C:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C:13]2([CH2:18][CH:19]([CH2:23][O:24][CH2:25][CH2:26][OH:27])[C:20]([OH:22])=[O:21])[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:5]1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 178496220HCID 178496220, compound

Product 1

HCID 178525614HCID 178525614, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{1-[(cis-4-Carboxy-cyclohexyl)carbamoyl]-cyclopentyl}-2-[2-(methoxy)ethoxymethyl]propanoic acid (0.80 g, 2 mmole) was dissolved in dry dichloromethane (15 ml) and treated with trimethylsilyl iodide (1.4 ml, 10 mmole) at 0° C. under nitrogen. After 6 hours at 0° C., the reaction was poured into ice-cold dilute sodium hydrogen carbonate and washed with dichloromethane. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (3×50 ml). The first extract contained starting material, the second and third extracts were combined, washed with dilute sodium thiosulphate, dried (Na2SO4) and evaporated to give an orange oil. The residue was azeotroped with dichloromethane and washed with dichloromethane to give the title compound as a glassy foam (0.22 g, 29%). Found: C,57.24; H,8.07; N,3.42. C19H31NO7. 0.1 CH2Cl2 0.25 H2O requires C,57.58; H,8.02; N,3.52%.

Workup

  1. additionthe reaction was poured into ice-cold dilute sodium hydrogen carbonate
  2. washwashed with dichloromethane
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. extractionThe first extract
  5. washwashed with dilute sodium thiosulphate
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give an orange oil
  9. customThe residue was azeotroped with dichloromethane
  10. washwashed with dichloromethane

Sources & evidence

ORD record
ord-f1b9d6bcb3b742ffa2a74fb5e84cc06a
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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