HCID 86759037, compound → HCID 86759036, compound

HRID 492661Notes

Reaction equation

[CH3:1][C:2]([CH2:104][CH2:105][CH2:106][NH:107][C:108]([O:110][C:111]([CH3:114])([CH3:113])[CH3:112])=[O:109])([NH:96][C:97]([O:99][C:100]([CH3:103])([CH3:102])[CH3:101])=[O:98])[CH2:3][CH2:4][CH2:5][N:6]([C:89]([O:91][C:92]([CH3:95])([CH3:94])[CH3:93])=[O:90])[CH2:7][CH:8]([C:56]([CH2:78][CH2:79][CH2:80][NH:81][C:82]([O:84][C:85]([CH3:88])([CH3:87])[CH3:86])=[O:83])([CH2:66][CH2:67][CH2:68][CH2:69][NH:70][C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])[N:57]([CH3:65])[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:55])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][N:52]=[N+]=[N-].[H][H]>C(O)(C)(C)C.[Pd]>[CH3:1][C:2]([CH2:104][CH2:105][CH2:106][NH:107][C:108]([O:110][C:111]([CH3:114])([CH3:113])[CH3:112])=[O:109])([NH:96][C:97]([O:99][C:100]([CH3:103])([CH3:102])[CH3:101])=[O:98])[CH2:3][CH2:4][CH2:5][N:6]([C:89]([O:91][C:92]([CH3:93])([CH3:94])[CH3:95])=[O:90])[CH2:7][CH:8]([C:56]([CH2:78][CH2:79][CH2:80][NH:81][C:82]([O:84][C:85]([CH3:86])([CH3:87])[CH3:88])=[O:83])([CH2:66][CH2:67][CH2:68][CH2:69][NH:70][C:71]([O:73][C:74]([CH3:75])([CH3:76])[CH3:77])=[O:72])[N:57]([CH3:65])[C:58]([O:60][C:61]([CH3:62])([CH3:63])[CH3:64])=[O:59])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:55])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][NH2:52]

Participants

Conditions

Temperature: 40 °C

Procedure

To E7 (184 mg) dissolved in tert-butanol at 40° C. was added Pd/C (50 mg) and the atmosphere changed to hydrogen. The hydrogenation was heated at 40° C. for 3 days, the catalyst filtered off and the solvent removed. The residues were purified by silica chromatography eluting initially with 100:10:0 CH2Cl2:MeOH:NH4OH to remove faster running impurities then with 100:10:1 to remove the title compound as a colourless gum, 61 mg, 34%. C91H178N8O13 requires 1591.3. Found ES+: MH+, 1592.3. δH (CDCl3) 1.24 (72H, br, H2N(CH2)2(CH2)32, CONH(CH2)2(CH2)4), 1.44 (66H, br, (Me)3C, CH2CH2N), 1.72 (4H, p, NCH2CH2CH2N), 1.98 (1H, br, CH), 2.14 (2H, t, CH2CO), 2.67 (2H, t, CH2NH2), 2.83 (6H, s, NMe), 2.95-3.30 (22H, m, NCH2), 5.62 (1H, br, CONH(CH2)6CH).

Workup

filtrationthe catalyst filtered off
customthe solvent removed
customThe residues were purified by silica chromatography
washeluting initially with 100:10:0 CH2Cl2
customMeOH:NH4OH to remove faster
customwith 100:10:1 to remove the title compound as a colourless gum, 61 mg, 34%

Sources & evidence

ORD record: ord-50c7c31598e24ae583b147df014a844d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531676B2

Reaction notes

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