1-Hydroxybenzotriazole → [4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl Ester

HRID 348674Notes

Reaction equation

HRID 348674 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:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=1)[CH2:45][CH2:46][CH3:47])[CH2:42][CH3:43]>C(Cl)(Cl)Cl.CN(C=O)C>[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:55][C:52]2[CH:53]=[CH:54][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 4

HCID 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 109.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In chloroform (20 ml) and DMF (8.0 ml), 4-(t-butoxycarbonylaminomethyl)benzoic acid (1.95 g) was dissolved. Then, the solution was added with WSCI hydrochloride (1.50 g) and HOBt (1.08 g), followed by stirring at room temperature at 1 hour. The reaction solution was added with the compound (1.23 g) obtained in Example 19-2 and chloroform (10 ml), followed by stirring at room temperature for 15 hours. The solvent was distilled off and the residue obtained was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (2.86 g) as a yellow oily substance.

Workup

  1. stirringby stirring at room temperature for 15 hours
  2. distillationThe solvent was distilled off
  3. customthe residue obtained
  4. customwas then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-0b1fe2bc5f8443d2ac916cbb730ffeb1
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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