2-[2-(2-Methoxyethoxy)ethoxy]acetyl chloride → 11,22,33-Tris(benzyloxy)-12,15,23,26,34-pentaoxo-11,16,22,27,33-pentaaza-2,5,8,36,39,42-hexaoxatritetracontane

HRID 2380437Notes

Reaction equation

HRID 2380437 reaction equation
[CH2:1]([O:8][N:9]([C:20](=[O:61])[CH2:21][CH2:22][C:23](=[O:60])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:31](=[O:51])[CH2:32][CH2:33][C:34](=[O:50])[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:62](Cl)(=[O:72])[CH2:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69][O:70][CH3:71]>>[CH2:1]([O:8][N:9]([C:20](=[O:61])[CH2:21][CH2:22][C:23](=[O:60])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:31](=[O:51])[CH2:32][CH2:33][C:34](=[O:50])[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:62](=[O:72])[CH2:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69][O:70][CH3:71])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27595712-[2-(2-Methoxyethoxy)ethoxy]acetyl chlorideHCID 1510174111,22,33-Tris(benzyloxy)-12,15,23,26-tetraoxo-11,16,22,27,33-pentaaza-2,5,8-trioxatritriacontane

Product 1

HCID 1510174311,22,33-Tris(benzyloxy)-12,15,23,26,34-pentaoxo-11,16,22,27,33-pentaaza-2,5,8,36,39,42-hexaoxatritetracontaneYield 78%

Procedure

11,22,33-Tris(benzyloxy)-12,15,23,26,34-pentaoxo-11,16,22,27,33-pentaaza-2,5,8,36,39,42-hexaoxatritetracontane (23) was synthesized by reacting compound (21) (3.91 g, 4.60 mmol) with 3,6,9-trioxadecanoyl chloride [Helmann, supra] (NEt3 /CH2C12) to give 4.0 g (78%) of (23): NMR δ 1.17-1.78 (m, 12 H), 2.3-2.9 (m, 8 H), 3.04-3.37 (m, 10 H), 3.4-3.8 (m, 24 H), 4.21 (s, 2 H), 4.76 (s, 2 H), 4.81 (s, 2 H), 4.88 (s, 2 H), 6.17-6.37 (m, 2 H), 7.34 (s, 15 H). Analysis: (C53H79N5O14) C, H, N.

Workup

  1. custom11,22,33-Tris(benzyloxy)-12,15,23,26,34-pentaoxo-11,16,22,27,33-pentaaza-2,5,8,36,39,42-hexaoxatritetracontane (23) was synthesized

Sources & evidence

ORD record
ord-35df8019d14c4f56bd0def06ebe5a772
Source dataset
uspto-grants-1994_11
Patent number
US05367113

Reaction notes

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