Sodium Hydroxide → [4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl Ester

HRID 2080756Notes

Reaction equation

HRID 2080756 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH2:41]([N:44]([CH2:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH3:47])[CH2:42][CH3:43].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:53][C:52]2[CH:54]=[CH:55][C:49]([CH2:48][N:44]([CH2:45][CH2:46][CH3:47])[CH2:41][CH2:42][CH3:43])=[CH:50][CH:51]=2)=[CH:17][CH:18]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167770114-Dipropylaminomethyl-aniline

Product 1

HCID 66941656[4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl EsterYield 29.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Commercially available 4-(t-butoxycarbonylamino-methyl)-benzoic acid (manufactured by Watanabe Chemical Industries, Ltd.) (1.16 g) was dissolved in chloroform (20 ml) and then added with WSCI hydrochloride (1.21 g), HOBt (963 mg), and the compound (865 mg) obtained in Example 15-2, and the whole was stirred overnight at room temperature. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added thereto and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (545 mg) as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. extractionThe solution was subjected to extraction with chloroform
  3. washwashed with a saturated aqueous ammonium chloride solution
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-ee52706acc1e4155a19c975f91457c41
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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