Veratrylamine → HCID 9082705, compound

HRID 1455727Notes

Reaction equation

HRID 1455727 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].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][C:51]=1[O:52][CH3:53])[CH2:47][NH2:48].C(N(C(C)C)C(C)C)C>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:48][CH2:47][C:46]2[CH:49]=[CH:50][C:51]([O:52][CH3:53])=[C:44]([O:43][CH3:42])[CH:45]=2)=[O:16])=[CH:17][CH:18]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 9082705HCID 9082705, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (1.0 g, 4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (920 mg, 4.8 mmol), 1-hydroxybenzotriazole hydrate (600 mg, 4.4 mmol), 3,4-dimethoxybenzylamine (730 mg, 4.4 mmol) and N-ethyldiisopropylamine (2.5 ml, 14 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate. This solution was washed with 1N hydrochloric acid (2×), sodium bicarbonate solution (2×) and sodium chloride solution. The solution was dried over magnesium sulphate and evaporated under reduced pressure to afford the title compound as a colourless solid, 1.6 g.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThis solution was washed with 1N hydrochloric acid (2×), sodium bicarbonate solution (2×) and sodium chloride solution
  4. dry with materialThe solution was dried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-33a965a341dc40f1bccbcfdf0733cb5c
Source dataset
uspto-grants-2009_01
Patent number
US07482487B2

Reaction notes

Loading…