Imidazole → HCID 86759019, compound

HRID 1370237Notes

Reaction equation

HRID 1370237 reaction equation
[CH3:1][C:2]1([CH3:38])[O:7][C@@H:6]([O:8][C:9]2[CH:32]=[CH:31][C:12]3[C:13]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15](=[O:17])[O:16][C:11]=3[C:10]=2[CH3:33])[C@H:5]([OH:34])[C@H:4]([OH:35])[C@H:3]1[O:36][CH3:37].C(N(C(C)C)CC)(C)C.N1C=CN=C1.[CH2:53]([Si:55]([CH2:59][CH3:60])([CH2:57][CH3:58])Cl)[CH3:54].P([O-])(O)(O)=O.[Na+]>C(Cl)Cl>[CH3:38][C:2]1([CH3:1])[O:7][C@@H:6]([O:8][C:9]2[CH:32]=[CH:31][C:12]3[C:13]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15](=[O:17])[O:16][C:11]=3[C:10]=2[CH3:33])[C@H:5]([OH:34])[C@H:4]([O:35][Si:55]([CH2:59][CH3:60])([CH2:57][CH3:58])[CH2:53][CH3:54])[C@H:3]1[O:36][CH3:37]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 81531DiisopropylethylamineHCID 23672064Monosodium phosphateHCID 86759020HCID 86759020, compound

Product 1

HCID 86759019HCID 86759019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

50 g of a solution from stage A in 500 ml of methylene chloride is agitated under arcon at ambient temperature. 42 ml of diisopropylethylamine and 9.66 g of imidazole are added. The solution is agitated for 15 minutes or cooled down to 0° C., 20.64 ml of triethylchlorosilane is added dropwise over 30 minutes, and agitation is carried out for 2 hours at 0° C. The reaction medium is poured into a molar solution of sodium dihydrogen phosphate. Extraction is carried out with methylene chloride followed by drying and evaporating to dryness. 66.27 g of product is recovered that is purified on silica eluting with a methylene chloride mixture at 0.75% of acetone. When the product is nearly isolated,, eluting is carried out with a methylene chloride solution at 1% of acetone. 41.04 g of sought product is obtained after saponification in a hexane/ethyl acetate mixture (9-1).

Workup

  1. waitagitation is carried out for 2 hours at 0° C
  2. extractionExtraction
  3. customby drying
  4. customevaporating to dryness
  5. custom66.27 g of product is recovered
  6. customthat is purified on silica eluting with a methylene chloride mixture at 0.75% of acetone
  7. customWhen the product is nearly isolated
  8. washeluting

Sources & evidence

ORD record
ord-a27c3799e4d74e57a30651597533a470
Source dataset
uspto-grants-2003_06
Patent number
US06583119B2

Reaction notes

Loading…