Citric Acid → HCID 131722140, compound

HRID 2119829Notes

Reaction equation

HRID 2119829 reaction equation
[CH2:1]([O:5][C:6]([NH:8][C:9]([CH3:22])([CH3:21])[CH2:10][CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].N1CCCCC1.ON1[C:34]2[CH:35]=[CH:36][CH:37]=C[C:33]=2[N:32]=[N:31]1.C(N(C(C)C)CC)(C)C.CN(CCCN=C=NCC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.C(OCC)(=O)C>[N:32]1([NH:31][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][C:9]([CH3:22])([NH:8][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[CH3:21])=[CH:20][CH:19]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

9

Reactant 6

HCID 311Citric AcidHCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 69584287HCID 69584287, compound

Product 1

HCID 131722140HCID 131722140, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a flame dried flask under a nitrogen atmosphere was added N-butyloxycarbonyl-4-(3-methyl-3-aminobutyl) benzoic acid (500 mg), piperidine (0.161 mL, 1.0 eq.), 1-hydroxybenzotriazole (47 mg, 1.0 eq.), diisopropylethylamine (0.2 mL, 3.5 eq.), and 25 mL of methylene chloride. A solution of (dimethylaminopropyl)ethyl carbodiimide in 20 mL of methylene chloride was then added and the resulting solution was allowed to stir for 1 hour before diluting with ethyl acetate. This mixture was acidified with 10% aqueous citric acid. The organics were washed twice each with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in ethyl acetate and was washed twice with 10% aqueous sodium bicarbonate, once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound.

Workup

  1. customTo a flame dried flask under a nitrogen atmosphere
  2. washThe organics were washed twice each with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washwas washed twice with 10% aqueous sodium bicarbonate, once with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfdbfdea06534916bdb91aec6a5d4ec0
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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