Acetic Anhydride → 6,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrile

HRID 1109847Notes

Reaction equation

HRID 1109847 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][N:16]([C:23](=[O:52])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1.C(Cl)Cl>[CH2:8]([O:15][N:16]([C:23](=[O:52])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][N:34]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:1](=[O:3])[CH3:2])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 99862666,12,18-Tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile

Product 1

HCID 101008386,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrileYield 60%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetic anhydride (8 mL) was slowly added to a solution of (8) (1.25 g, 2.03 mmol) in pyridine (50 mL) and CH2Cl2 (30 mL) which had been cooled to 0° C. Stirring was continued at 0° C. for 30 minutes and then at room temperature overnight. Solvents were removed under high vacuum, and the residue was dissolved in CHCl3 (120 mL), followed by washing with 0.5N HCl (2×40 mL) and saturated NaHCO3 (2×40 mL). After solvent removal, the crude oil was purified by silica gel column chromatography, eluting with 3:1 EtOAc/hexane, to furnish 0.8 g (60%) of (9) as an oil: NMR δ 1.40-1.80 (m, 12 H), 2.05 (s, 3 H), 2.20-2.50 (m, 6 H), 3.40-3.73 (m, 6 H), 4.75 (s, 6 H) , 7.32 (s, 15 H). Anal. (C38H48N4O6) C, H, N.

Workup

  1. customat room temperature
  2. customovernight
  3. customSolvents were removed under high vacuum
  4. dissolutionthe residue was dissolved in CHCl3 (120 mL)
  5. washby washing with 0.5N HCl (2×40 mL) and saturated NaHCO3 (2×40 mL)
  6. customAfter solvent removal
  7. customthe crude oil was purified by silica gel column chromatography
  8. washeluting with 3:1 EtOAc/hexane

Sources & evidence

ORD record
ord-215dcef00ec74818b619f710d9eaf4cb
Source dataset
uspto-grants-1994_06
Patent number
US05322961

Reaction notes

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