Acetic Anhydride → HCID 11051114, compound

HRID 1656820Notes

Reaction equation

HRID 1656820 reaction equation
[CH2:1]([O:8][N:9]([C:16](=[O:57])[CH2:17][CH2:18][C:19](=[O:56])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:27](=[O:47])[CH2:28][CH2:29][C:30](=[O:46])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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:58](OC(=O)C)(=[O:60])[CH3:59]>N1C=CC=CC=1>[CH2:1]([O:8][N:9]([C:16](=[O:57])[CH2:17][CH2:18][C:19](=[O:56])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:27](=[O:47])[CH2:28][CH2:29][C:30](=[O:46])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N:37]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:58](=[O:60])[CH3:59])[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

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15101733HCID 15101733, compound

Product 1

HCID 11051114HCID 11051114, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6,17,28-Tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile (13) was prepared by dissolving compound (12) (1.1 g, 1.4 mmol) in pyridine (16 mL), adding acetic anhydride (4 mL) and stirring the solution for 12 hours. After removal of solvents under high vacuum, water was added, followed by extraction with CHCl3. The organic extracts were washed with 1N HCl and saturated NaHCO3. Column chromatography (5% CH3OH/CHCl3) gave 1.05 g (91%) of (13): NMR δ 1.4-1.59 (m, 4 H), 1.59-1.70 (m, 6 H), 1.70-1.85 (m, 6 H), 2.1 (s, 3 H), 2.35 (t, 2 H), 2.40-2.55 (m, 4 H), 2.75-2.90 (m, 4 H), 3.18-3.28 (m, 4 H), 3.6-3.7 (m, 6 H), 4.8 (s, 2 H), 4.82 (s, 2 H), 4.84 (s, 2 H), 6.20-6.75 (m, 2 H), 7.4 (s, 15 H). Anal. calcd. for C46H62N6O8 : C, 66.30; H, 7.68. Found: C, 66.44; H, 7.66 [Bergeron at al, J. Org. Chem., supra].

Workup

  1. custom6,17,28-Tris(benzyloxy)-7,10,18,21,29-pentaoxo-6,11,17,22,28-pentaazatriacontanenitrile (13) was prepared
  2. customAfter removal of solvents under high vacuum, water
  3. additionwas added
  4. extractionfollowed by extraction with CHCl3
  5. washThe organic extracts were washed with 1N HCl and saturated NaHCO3

Sources & evidence

ORD record
ord-e7a100b77a8944c28327317af1a54d0b
Source dataset
uspto-grants-1993_10
Patent number
US05254724

Reaction notes

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