Sodium Hydroxide → HCID 53951774, compound

HRID 1904149Notes

Reaction equation

HRID 1904149 reaction equation
[OH-].[Na+].[I:3][CH2:4][CH2:5][O:6][N:7]=[C:8]([C:14]1[N:15]=[C:16]([NH:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:17][CH:18]=1)[C:9]([O:11]CC)=[O:10]>O1CCOCC1.C(O)C>[I:3][CH2:4][CH2:5][O:6][N:7]=[C:8]([C:14]1[N:15]=[C:16]([NH:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:17][CH:18]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54296994HCID 54296994, compound

Product 1

HCID 53951774HCID 53951774, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

5.5 ml of a 2 N sodium hydroxide solution was added dropwise under an inert atmosphere to a mixture of 6.7 g of the product of Step A in 5.5 ml of dioxane and 44 ml of absolute ethanol and after the addition of 7 ml of absolute ethanol the mixture was stirred overnight to room temperature and was vacuum filtered. The recovered product was rinsed twice with 3 ml of a 4-1 ethanol-dioxane mixture and was then empasted with ether. The product was placed in a mixture of 100 ml of water and 100 ml of chloroform and the pH was adjusted to 2 by addition of N hydrochloric acid. The decanted organic phase was washed with an aqueous saturated sodium chloride solution, was dried and evaporated to dryness under reduced pressure. The residue was dissolved in 35 ml of dichloroethane at 40° C. and crystallization was induced. The mixture stood at room temperature for 72 hours and was vacuum filtered. The recovered product was rinsed and dried to obtain 5.4 g of the syn isomer of 2-(2-iodoethoxyimino)-2-(2-tritylamino-4-thiazolyl)-acetic acid solvated with dichloroethane melting at 161° C. (= to 4.61 g of pure product).

Workup

  1. filtrationfiltered
  2. washThe recovered product was rinsed twice with 3 ml of a 4-1 ethanol-dioxane mixture
  3. additionThe product was placed in a mixture of 100 ml of water and 100 ml of chloroform
  4. additionthe pH was adjusted to 2 by addition of N hydrochloric acid
  5. washThe decanted organic phase was washed with an aqueous saturated sodium chloride solution
  6. customwas dried
  7. customevaporated to dryness under reduced pressure
  8. dissolutionThe residue was dissolved in 35 ml of dichloroethane at 40° C.
  9. customcrystallization
  10. filtrationfiltered
  11. washThe recovered product was rinsed
  12. customdried

Sources & evidence

ORD record
ord-b2e28c5f172f40e6a641bb18fa7141aa
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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