Veratric Acid → HCID 59773004, compound

HRID 2220685Notes

Reaction equation

HRID 2220685 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.Cl.C(N=C=N[CH2:20][CH2:21][CH2:22][N:23]([CH3:25])C)C.C(N([CH2:31][CH3:32])CC)C.ON1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.[C:43]([O:47][C:48]([N:50]1[CH2:54][CH2:53][CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:43]([O:47][C:48]([N:50]1[CH2:54][CH2:53][CH2:52][C@H:51]1[CH2:25][N:23]([C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:22][C:21]1[CH:20]=[CH:32][C:31]2[C:42](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:41]=1)=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

8

Reactant 6

HCID 7121Veratric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 643455N-Boc-pyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59773004HCID 59773004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dimethoxy benzoic acid 1.04 g (5.72 mmol) was dissolved in 30 mL tetrahydrofuran, to this mixture was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 1.4 g (6.6 mmol), triethylamine 0.66 g (5.72 mmol), after 30 minutes 1-hydroxybenzotriazole 0.77 g (5.72 mmol) was added. The mixture was stirred one hour. To this mixture was added 2-{[naphthalen-2-ylmethyl]-amino]-methyl}-pyrrolidin-1-carboxylic acid tert-butyl ester 1.5 g (4.4 mmol). The mixture was stirred 1 night at room temperature. Added 50 mL of saturated sodium bicarbonate and extract with ethyl acetate 3 times 100 mL. The combined organic layer was dried over magnesium sulfate, filtered, and concentrated under vacuum. Purification over silica gel hexane: 1-dichloromethane: 1, lead to 1.1 g white powder. LC-MSD, m/z for: C30H36N2O5 [M+H]: 505.2. LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 7 minutes: 5.0 min.

Workup

  1. additionTo this mixture was added 2-{[naphthalen-2-ylmethyl]-amino]-methyl
  2. stirringThe mixture was stirred 1 night at room temperature
  3. extractionextract with ethyl acetate 3 times 100 mL
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification over silica gel hexane
  8. waitLC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 7 minutes
  9. custom5.0 min.

Sources & evidence

ORD record
ord-6db0e16528f64b299c8d636fccf75c45
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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