Dicyclohexylcarbodiimide → 4-((3-(4-(4-(12-Bromododecyloxy)benzoyloxy)benzoyloxy)phenoxy)carbonyl)phenyl 4-(dodecyl-oxy)benzoate

HRID 417789Notes

Reaction equation

HRID 417789 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:39]=[CH:38][C:18]([C:19]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=3)=[O:29])=[CH:24][CH:23]=2)=[O:20])=[CH:17][CH:16]=1.[CH2:40]([O:52][C:53]1[CH:70]=[CH:69][C:56]([C:57]([O:59][C:60]2[CH:68]=[CH:67][C:63]([C:64](O)=[O:65])=[CH:62][CH:61]=2)=[O:58])=[CH:55][CH:54]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CC(=O)OCC>[CH2:40]([O:52][C:53]1[CH:54]=[CH:55][C:56]([C:57]([O:59][C:60]2[CH:68]=[CH:67][C:63]([C:64]([O:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([O:30][C:28](=[O:29])[C:25]4[CH:24]=[CH:23][C:22]([O:21][C:19](=[O:20])[C:18]5[CH:38]=[CH:39][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[CH:16][CH:17]=5)=[CH:27][CH:26]=4)[CH:32]=3)=[O:65])=[CH:62][CH:61]=2)=[O:58])=[CH:69][CH:70]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 158098334-{[4-(Dodecyloxy)benzoyl]oxy}benzoic acidHCID 666483614-((3-Hydroxyphenoxy)carbonyl)phenyl 4-(12-bromododecyloxy)benzoate

Product 1

HCID 866519244-((3-(4-(4-(12-Bromododecyloxy)benzoyloxy)benzoyloxy)phenoxy)carbonyl)phenyl 4-(dodecyl-oxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Synthesized as described for the preparation of compound BC1. Quantities: 25 (0.15 g, 0.25 mmol), 17 (0.11 g, 0.25 mmol), DMAP (0.03 g, 0.25 mmol), DCC (0.10 g, 0.5 mmol). Yield 0.18 g (72%). EA: Found: C, 69.39; H, 7.13. C58H69BrO10 requires C, 69.24; H, 6.91%. 1H NMR: δH (CDCl3; 300 MHz): 0.91 (3 H, t, 3J=6.8 Hz, CH3), 1.19-1.56 (34 H, m, CH2), 1.85 (6 H, m, O—CH2—CH2/Br—CH2—CH2), 3.43 (2 H, t, 3J=6.8 Hz, CH2Br), 4.08 (4 H, t, 3J=6.5 Hz, OCH2), 7.01 (2 H, d, 3J=8.8 Hz, Ar—H), 7.21 (3 H, m, Ar—H), 7.40 (4 H, d, 3J=8.6 Hz, Ar—H), 7.52 (1 H, t, 3J=8.1 Hz, Ar—H), 8.18 (4 H, d, 3J=8.8 Hz, Ar—H), 8.30 (4 H, d, 3J=8.6 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 14.5, 23.1, 26.4, 28.6, 29.2, 29.5, 29.75, 29.8, 29.85, 29.9, 29.95, 30.0, 32.3, 33.2, 34.4, 68.8, 114.7, 114.8, 116.2, 119.7, 121.4, 122.5, 127.0, 130.2, 132.2, 132.25, 132.3, 132.8, 151.8, 151.85, 155.9, 164.2, 164.5, 164.7. m/z (MALDI) 1028.00 (100%) and 1030.03 (97%) [M+Na]+, C58H69BrNaO10 requires 1027.40 (100%) and 1029.40 (97%).

Workup

  1. customSynthesized
  2. customas described for the preparation of compound BC1

Sources & evidence

ORD record
ord-4999e0d472794051afd2d67c4e34a16f
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

Loading…