6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid → HCID 67103490, compound

HRID 2080828Notes

Reaction equation

HRID 2080828 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH2:11]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](O)=[O:28])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:11]([O:18][C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](=[O:28])[NH:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[NH2:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 757711-HydroxybenzotriazoleHCID 7372853,4-DiaminobenzonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67103490HCID 67103490, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The compound (510 mg) obtained in Example 46-1 was dissolved in DMF (20 ml). To this solution, a solution which was previously prepared by dissolving 6-benzyloxycarbonylamino-hexanoic acid (1.10 g) in DMF (10 ml), adding thereto WSCI hydrochloride (1.08 g) and HOBt (762 mg), and stirring the mixture for 30 minutes was dropped. The whole was stirred for 20 hours. The residue obtained by distilling the solvent off was subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution, and dried with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (961 mg) as a white solid.

Workup

  1. customTo this solution, a solution which was previously prepared
  2. additionadding
  3. additionwas dropped
  4. customThe residue obtained
  5. distillationby distilling the solvent
  6. extractionoff was subjected to extraction with chloroform
  7. washThe organic layer was washed with water
  8. dry with materiala saturated saline solution, and dried with anhydrous sodium sulfate
  9. customThe residue obtained
  10. distillationby distilling the solvent
  11. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-dd2ade0f10184013aff11958b9517bc6
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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