2,6-Dimethoxybenzoic Acid → HCID 57748833, compound

HRID 598503Notes

Reaction equation

HRID 598503 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([OH:7])=O.C(OC(=O)[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:5]([C:4]2[C:8]([O:12][CH3:13])=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[O:7])[CH2:22]1

Participants

6

Reactant 4

HCID 151092,6-Dimethoxybenzoic AcidHCID 81531DiisopropylethylamineHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 57748833HCID 57748833, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.143 g (0.786 mmol) 2,6-dimethoxybenzoic acid (commercially available), 0.15 g (0.749 mmol) (R)-piperidin-3-yl-carbamic acid tert-butyl ester (commercially available), 0.264 g (0.824 mmol) TBTU and 0.145 g (1.123 mmol) DIPEA in 9.2 mL DMF was stirred at room temperature over night. DMF was evaporated and the residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid. The product containing fractions were evaporated and the residue was treated with 4N HCl in dioxane and stirred at 50° C. over night. The mixture was evaporated to dryness and treated with NaHCO3 aq. and DCM. The organic layer was separated, dried with MgSO4 and evaporated to yield 22 mg (11%) of the title compound as colourless oil. (MH+) 265.1.

Workup

  1. customDMF was evaporated
  2. customthe residue was purified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. additionThe product containing fractions
  6. customwere evaporated
  7. additionthe residue was treated with 4N HCl in dioxane
  8. stirringstirred at 50° C. over night
  9. customThe mixture was evaporated to dryness
  10. additiontreated with NaHCO3 aq. and DCM
  11. customThe organic layer was separated
  12. dry with materialdried with MgSO4
  13. customevaporated

Sources & evidence

ORD record
ord-43329ac7e4184686b7d5d1babcb386de
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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