Succinic anhydride → HCID 10101221, compound

HRID 2396608Notes

Reaction equation

[CH2:1]([O:8][N:9]([C:23](=[O:43])[CH2:24][CH2:25][C:26](=[O:42])[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:44]1(=[O:50])[O:49][C:47](=[O:48])[CH2:46][CH2:45]1>N1C=CC=CC=1>[CH2:35]([O:34][N:33]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][NH:27][C:26](=[O:42])[CH2:25][CH2:24][C:23](=[O:43])[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][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:44](=[O:50])[CH2:45][CH2:46][C:47]([OH:49])=[O:48])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 81 °C

Procedure

A mixture of (9) (2.2 g, 3.48 mmol), succinic anhydride (0.55 g, 5.5 mmol) and pyridine (70 mL) was heated at 81° C. for 2 hours. Solvent was removed in vacuo and cold 1N HCl (100 mL) was added. Extraction was carried out with CHCl3 (6×75 mL), followed by a water wash (100 mL). Solvent removal and flash column chromatography, eluting with 7% MeOH/CH2Cl2, afforded 1.98 g (81%) of (10) as an oil: 300 MHz NMR δ 1.2-1.7 (m+s, 21 H), 2.53 (t, 2 H, J=7), 2.67 (s, 4 H), 2.78-2.86 (m, 2 H), 3.02-3.11 (m, 2 H), 3.22 (q, 2 H, J=6), 3.56-3.77 (m, 4 H), 4.7 (br s, 1 H), 4.83 (s, 2 H), 4.86 (s, 2 H) , 6.73 (br s, 1 H) , 7.38 (s, 10 H) . Anal. calcd. for C37H54N4O9 : C, 63.59; H, 7.79; N, 8.02. Found: C, 63.4 5; H, 7.81; N, 8.07.

Workup

customSolvent was removed in vacuo and cold 1N HCl (100 mL)
additionwas added
extractionExtraction
washwash (100 mL)
customSolvent removal and flash column chromatography
washeluting with 7% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-a7c04b1664a64603b737a9d6c4399cdb
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05493053

Reaction notes

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