4-(Benzyloxy)benzoic acid → HCID 18172425, compound

HRID 397030Notes

Reaction equation

HRID 397030 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][NH2:8].[CH2:12]([O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:25])=[CH:27][CH:28]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 738804-(Benzyloxy)benzoic acidHCID 748663-MethoxyphenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18172425HCID 18172425, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-methoxyphenethylamine (16.557 g, 109.5 mmol), 4-benzyloxybenzoic acid (25.000 g, 109.5 mmol), 1-hydroxybenzotriazole hydrate (22.202 g, 164.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (22.047 g, 115.0 mmol) in anhydrous CH2Cl2 (300 ml) was stirred at 0° C. under N2 for 1 hr, then warmed to rt and stirred at rt for 19 hr. The reaction mixture was washed sequentially with 1M NaOH (150 ml), 1M HCl (150 ml), and H2O (150 ml), then dried over MgSO4 and concentrated in vacuo to give 39.00 g (99% yield) of yellow solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 19 hr
  3. washThe reaction mixture was washed sequentially with 1M NaOH (150 ml), 1M HCl (150 ml), and H2O (150 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-abb1a263d0a2441b952b09a0faa354e3
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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