Dicyclohexylcarbodiimide → 4-((3-(4-(4-(12-Bromododecyloxy)benzoyloxy)benzoyloxy)phenoxy)carbonyl)phenyl 4-(12-(ethoxycarbonothioylthio)dodecyloxy)benzoate

HRID 417790Notes

Reaction equation

HRID 417790 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:42][C:43]([S:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][O:58][C:59]1[CH:76]=[CH:75][C:62]([C:63]([O:65][C:66]2[CH:74]=[CH:73][C:69]([C:70](O)=[O:71])=[CH:68][CH:67]=2)=[O:64])=[CH:61][CH:60]=1)=[S:44])[CH3:41].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CC(=O)OCC>[CH2:40]([O:42][C:43]([S:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][O:58][C:59]1[CH:76]=[CH:75][C:62]([C:63]([O:65][C:66]2[CH:74]=[CH:73][C:69]([C:70]([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:71])=[CH:68][CH:67]=2)=[O:64])=[CH:61][CH:60]=1)=[S:44])[CH3:41]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 666483614-((3-Hydroxyphenoxy)carbonyl)phenyl 4-(12-bromododecyloxy)benzoateHCID 866519264-(4-(12-(Ethoxycarbonothioylthio)dodecyloxy)benzoyloxy)benzoic acid

Product 1

HCID 866519254-((3-(4-(4-(12-Bromododecyloxy)benzoyloxy)benzoyloxy)phenoxy)carbonyl)phenyl 4-(12-(ethoxycarbonothioylthio)dodecyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Synthesized as described for the preparation of compound BC1. Quantities: 25 (0.22 g, 0.37 mmol), 22 (0.20 g, 0.37 mmol), DMAP (0.045 g, 0.37 mmol), DCC (0.15 g, 0.73 mmol). Yield 0.25 g (61%). EA: Found: C, 64.49; H, 6.81. C61H73BrO11S2 requires C, 65.05; H, 6.53%. 1H NMR: δH (CDCl3; 300 MHz): 1.22-1.62 (35 H, m, CH2/O—CH2—CH3), 1.71 (2 H, m, S—CH2—CH2), 1.87 (6 H, m, O—CH2—CH2/Br—CH2—CH2), 3.13 (2 H, t, 3J=7.4 Hz, SCH2), 3.42 (2 H, t, 3J=6.8 Hz, CH2Br), 4.07 (4 H, t, 3J=6.5 Hz, OCH2), 4.66 (2 H, q, 3J=7.1 Hz, O—CH2—CH3), 7.01 (2 H, d, 3J=8.7 Hz, Ar—H), 7.21 (3 H, m, Ar—H), 7.40 (4 H, d, 3J=8.5 Hz, Ar—H), 7.51 (1 H, t, 3J=8.1 Hz, Ar—H), 8.17 (4 H, d, 3J=8.7 Hz, Ar—H), 8.30 (4 H, d, 3J=8.5 Hz, Ar—H). 13C NMR: δC (CDCl3; 75 MHz): 13.8, 26.0, 28.2, 28.3, 28.8, 28.9, 29.0, 29.3, 29.35, 29.4, 29.5, 31.7, 32.8, 34.0, 35.9, 53.8, 68.4, 69.5, 69.7, 114.4, 115.8, 119.3, 120.9, 122.1, 126.6, 129.9, 131.9, 132.4, 151.4, 155.5, 163.8, 164.1, 164.3, 210.8. m/z (MALDI) 1147.56 (100%) and 1149.59 (97%) [M+Na]+, C61H73BrNaO11S2 requires 1147.37 (100.0%) and 1149.37 (97%).

Workup

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

Sources & evidence

ORD record
ord-8168323fe3184d62952112be53344b6f
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Reaction notes

Loading…