Syringic Acid → HCID 18510866, compound

HRID 1370545Notes

Reaction equation

HRID 1370545 reaction equation
[C:1]([OH:14])(=O)[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH:38]1([N:44]2[CH2:52][C:51]3[C:46](=[CH:47][C:48]([N:53]4[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]4)=[CH:49][CH:50]=3)[C:45]2=[O:59])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.[Cl-].[NH4+]>CN(C=O)C.C(N(CC)CC)C>[CH:38]1([N:44]2[CH2:52][C:51]3[C:46](=[CH:47][C:48]([N:53]4[CH2:54][CH2:55][N:56]([C:1](=[O:14])[C:2]5[CH:3]=[C:4]([O:5][CH3:6])[C:7]([OH:8])=[C:9]([O:10][CH3:11])[CH:12]=5)[CH2:57][CH2:58]4)=[CH:49][CH:50]=3)[C:45]2=[O:59])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Participants

8

Reactant 5

HCID 10742Syringic AcidHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22180413HCID 22180413, compound

Product 1

HCID 18510866HCID 18510866, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of syringic acid (20 mg) in dry DMF (2 ml) was cooled to 0° C. 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (WSCI) and 1-hydroxybenztriazole hydrate (HOBt) were added thereto in that order. The mixture was stirred at 0° C. for one hr. The compound (30 mg) obtained in step (e) of Example 1 and triethylamine were added thereto in that order. The mixture was stirred at 0° C. for one hr, and then stirred at room temperature overnight. A saturated aqueous ammonium chloride solution(5 ml) was added thereto, followed by separation with ethyl acetate and water. The ethyl acetate layer was washed with an aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under the reduced pressure. The residue was purified by chromatography on silica gel (chloroform:methanol=20:1) to give 42 mg of the title compound.

Workup

  1. stirringThe mixture was stirred at 0° C. for one hr
  2. stirringstirred at room temperature overnight
  3. customfollowed by separation with ethyl acetate and water
  4. washThe ethyl acetate layer was washed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under the reduced pressure
  7. customThe residue was purified by chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-bbe6e7d44a194c888a6d893446094ab4
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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