Hydrochloric Acid → HCID 76168100, compound

HRID 1836509Notes

Reaction equation

HRID 1836509 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]([CH2:5][O:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:8](=[O:18])[CH:9]=[C:10]1[C:14](=[O:15])[O:13]C(C)(C)[O:11]1)=[O:4].[OH-].[Li+].Cl>O1CCCC1>[CH3:27][N:2]([CH3:1])[C:3]([CH2:5][O:6][N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:8]([CH:9]=[C:10]([OH:11])[C:14]([OH:15])=[O:13])=[O:18])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 73855551HCID 73855551, compound

Product 1

HCID 76168100HCID 76168100, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-dimethylcarbamoylmethoxy-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-(4-fluorobenzyl)-acetamide (0.065 g, 0.17 mmol in tetrahydrofuran (3 ml) was treated at 0° C. with 0.34 ml (0.34 mmol) of 1 M aqueous lithium hydroxide. After 1 h, the reaction mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried (magnesium sulphate) and evaporated in vacuo. Crystallisation of the residual solid from a mixture of ethyl acetate and hexane gave 0.043 g (74% yield) of the title material as a white solid: mp 118-120° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm); (mixture of enol and keto forms, 7:3); enol form: 2.83 (3H, s, NCH3), 2.88 (3H, s, NCH3), 4.79 (2H, s, CH2), 4.94 (2H, s, CH2), 6.47 (1H, s, CH), 7.18 (2H, m, aromatics), 7.38 (2H, m, aromatics), 13.2 (1H, broad, OH), 13.7 (1H, broad, OH). HRMS (ES+) calculated for C15H18FN2O6[M+H]+: 341.114890. Found: 341.115095.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated in vacuo
  5. customCrystallisation of the residual solid
  6. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-8b097edaef5b48f3856e2b33cfb88853
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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