Hydrochloric Acid → HCID 69141166, compound

HRID 1794151Notes

Reaction equation

HRID 1794151 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:5]=1[CH2:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][C@H:11]1[CH2:23][CH3:24])=[O:9].[CH3:30]I.[ClH:32]>CN(C=O)C>[ClH:32].[F:3][C:4]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:5]=1[CH2:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][C@H:11]1[CH2:23][CH3:24])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69141315HCID 69141315, compound

Product 1

HCID 69141166HCID 69141166, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.27 mg (0.157 mmol) NaH (60% suspension in mineral oil) and 40 mg (0.105 mmol) (R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(2-fluoro-5-hydroxy-benzyl) ester in 1 ml DMF was stirred for 30 min at room temperature under argon. 16.4 mg (0.115 mmol) methyliodide was added and the mixture was stirred 30 min at room temperature. After addition of 60 ul HCl (37%) the mixture was purified with preparative HPLC eluting with an acetonitrile/water gradient. The fractions containing the desired intermediate were combined and 0.05 ml HCl (37%) was added before evaporation to dryness. The residue was taken up in 1 ml dioxane and 0.15 ml HCl (37%) and stirred for 30 min at 60° C. Evaporation of the mixture yielded 20 mg (57%) of the title compound. MS (ISP): 297 (M+H)+.

Workup

  1. stirringthe mixture was stirred 30 min at room temperature
  2. customwas purified with preparative HPLC
  3. washeluting with an acetonitrile/water gradient
  4. additionThe fractions containing the desired intermediate
  5. addition0.05 ml HCl (37%) was added before evaporation to dryness
  6. stirring0.15 ml HCl (37%) and stirred for 30 min at 60° C
  7. customEvaporation of the mixture

Sources & evidence

ORD record
ord-e86bf02d7c284acebf5d81cf30221656
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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