Nitrate → HCID 178418760, compound

HRID 11865

Reaction equation

HRID 11865 reaction equation
[NH2:1][CH2:2][C:3]1[CH:34]=[CH:33][C:6]([C:7]([NH:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)C(OC(C)(C)C)=O)[C:11]([OH:13])=[O:12])=[O:8])=[CH:5][CH:4]=1.[N+:35]([O-])([O-])=O.C([N:41]([CH2:44]C)CC)C>CN(C=O)C>[NH:1]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[C:11]([OH:13])=[O:12])=[O:8])=[CH:33][CH:34]=1)[C:44]([NH2:41])=[NH:35]

Participants

5

Reactant 3

HCID 943NitrateHCID 8471TriethylamineHCID 21043758(S)-2-((4-aminomethylbenzoyl)amino)-5-(N-Boc-2-picolylaminomethyl)valeric Acid

Product 1

HCID 178418760HCID 178418760, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 41-5 (0.01 g) was dissolved in DMF (0.3 ml). After the addition of dimethylpyrazolecarboxyamidine nitrate (0.01 g), the mixture was adjusted to pH 8 with triethylamine and stirred for 3 days. The reaction solution was concentrated. Chloroform was added to the residue and the mixture was washed with saturated aqueous solution of sodium hydrogencarbonate. The organic layer was concentrated and dried under reduced pressure. The residue was purified by silica gel column chromatography (5 g, chloroform/methanol/water=7/3/0.5) to obtain the title compound (0.01 g) as white foam. The foam was dissolved in methanol (0.3 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.3 ml) was added dropwise. The mixture was stirred for 3 hours at room temperature. The reaction solution was concentrated and dried under reduced pressure to obtain a crude product (0.01 g). The crude product was purified by silica gel column chromatography (0.5 g, chloroform/methanol/water=7/3/0.5) and 1 mol/l hydrochloric acid was added. The mixture was concentrated to obtain hydrochloride of the title compound (0.01 g) as white foam.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionChloroform was added to the residue
  3. washthe mixture was washed with saturated aqueous solution of sodium hydrogencarbonate
  4. concentrationThe organic layer was concentrated
  5. customdried under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (5 g, chloroform/methanol/water=7/3/0.5)

Sources & evidence

ORD record
ord-1b8da72fa0b543b09dd1bd7a4a052cdb
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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