HCID 86664854, compound → HCID 86664853, compound

HRID 1952518Notes

Reaction equation

HRID 1952518 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][N:66]1[C:74](=[O:75])[C:73]2[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=2)[C:67]1=[O:76])[C:20]([C:22]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][OH:35])[CH:29]=2)[C:25]([C:36]#[C:37][C:38]([OH:51])([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:24](/[CH:52]=[CH:53]/[C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:23]=1)=[O:21]>CCOC(C)=O.[Pd]>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][N:66]1[C:67](=[O:76])[C:68]2[C:73](=[CH:72][CH:71]=[CH:70][CH:69]=2)[C:74]1=[O:75])[C:20]([C:22]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][OH:35])[CH:29]=2)[C:25]([CH2:36][CH2:37][C:38]([OH:51])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[C:24]([CH2:52][CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:23]=1)=[O:21]

Participants

4

Reactant 1

HCID 86664854HCID 86664854, compound

Product 1

HCID 86664853HCID 86664853, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The compound 6 (4 mg) obtained above was subsequently reduced by passing H2 through a stirred suspension in EtOAc (2 mL) and 10% Pd—C (4 mg) for 6 hours (or until the reaction completed by NMR). The catalyst was filtered off (Celite), the filtrate was evaporated in vacuo to give 4 mg of the title compound as a crude mixture; 1H NMR (400 MHz, CDCl3) δ 7.82 (m, 4H), 7.70 (m, 4H), 7.20-7.32 (m, 14H), 6.10 (s, 1H), 5.10 (s, 2H), 4.56 (s, 2H), 4.04 (m, 2H), 3.64 (m 4H), 3.25 (m, 4H), 2.09-2.62 (m, 8H), and 1.17-1.62 (m, 23H).

Workup

  1. filtrationThe catalyst was filtered off (Celite)
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-d6ad567d1f9548f190706db7ef39a2a2
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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