Succinic anhydride → 5,16-Bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

HRID 2380433Notes

Reaction equation

HRID 2380433 reaction equation
[CH2:1]([O:8][N:9]([C:16](=[O:36])[CH2:17][CH2:18][C:19](=[O:35])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]1(=[O:43])[O:42][C:40](=[O:41])[CH2:39][CH2:38]1>N1C=CC=CC=1>[CH2:28]([O:27][N:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19](=[O:35])[CH2:18][CH2:17][C:16](=[O:36])[N:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:37](=[O:43])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 10929123N1-(4-Cyanobutyl)-N1-(phenylmethoxy)-N4-[5-[(phenylmethoxy)amino]pentyl]butanediamide

Product 1

HCID 111039395,16-Bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5,16-Bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid (10 ) was prepared by heating a solution of (9) (0.365 g, 0.738 mmol) and succinic anhydride (0.113 g, 1.13 mmol) in pyridine (10 mL) at 106° C. for 1.5 hours under N2. After removing the pyridine in vacuo, the residue was diluted with ether (25 mL) and then extracted with saturated NaHCO3 (3×25 mL). The combined aqueous portion was extracted further with ether (2×25 mL), then cautiously acidified with cold 6 N HCl (20 mL). Extraction with CHCl3 (3×40 mL), followed by a final water wash (40 mL) and solvent removal led to 0.424 g of (10) (96% yield): NMR δ 1.25-1.84 (m, 10 H), 2.2-2.92 (m, 10 H), 3.05-3.33 (m, 2 H), 3.5-3.8 (m, 4 H), 4.80 and 4.83 (2 s, 4 H), 6.6 (br s, 1 H), 7.34 (s, 10 H). Anal. calcd. for C32H42N4O7 : C, 64.63; H, 7.12; N, 9.42. Found: C, 64.70; H, 7.16; N, 9.39.

Workup

  1. custom5,16-Bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid (10 ) was prepared
  2. customAfter removing the pyridine in vacuo
  3. additionthe residue was diluted with ether (25 mL)
  4. extractionextracted with saturated NaHCO3 (3×25 mL)
  5. extractionThe combined aqueous portion was extracted further with ether (2×25 mL)
  6. extractionExtraction with CHCl3 (3×40 mL)
  7. washwash
  8. custom(40 mL) and solvent removal

Sources & evidence

ORD record
ord-2e3a28af07234a85a1053fccac996664
Source dataset
uspto-grants-1994_11
Patent number
US05367113

Reaction notes

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