HCID 86664856, compound → HCID 86664855, compound

HRID 1952525Notes

Reaction equation

HRID 1952525 reaction equation
[CH2:1]([N:8]1[C:12]([C:13](=[O:73])[NH:14][C:15]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]3[C:35](=[O:36])[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]3=[O:37])[C:18]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][N:45]3[C:53](=[O:54])[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:46]3=[O:55])=[C:17]([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][N:62]3[C:70](=[O:71])[C:69]4[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=4)[C:63]3=[O:72])[CH:16]=2)=[CH:11][C:10]([CH:74]=[CH:75][C:76]([O:78][CH2:79][CH3:80])=[O:77])=[C:9]1[C:81]#[C:82][C:83]([OH:96])([C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)[C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([N:8]1[C:12]([C:13](=[O:73])[NH:14][C:15]2[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]3[C:28](=[O:37])[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:35]3=[O:36])[C:18]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][N:45]3[C:46](=[O:55])[C:47]4[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:53]3=[O:54])=[C:17]([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][N:62]3[C:70](=[O:71])[C:69]4[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=4)[C:63]3=[O:72])[CH:16]=2)=[CH:11][C:10]([CH2:74][CH2:75][C:76]([O:78][CH2:79][CH3:80])=[O:77])=[C:9]1[C:81]#[C:82][C:83]([OH:96])([C:84]1[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=1)[C:90]1[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86664856HCID 86664856, compound

Product 1

HCID 86664855HCID 86664855, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 9 (0.07 g, 0.06 mmol) in EtOAc (20 mL) was added 10% dry Pd—C (0.007 g). The resulting mixture was stirred at room temperature for 48 hours under a H2 balloon. Pd—C was filtered off and the filtrate was concentrated to give 10 as colorless oil (0.06 g, 74%). The crude product was subjected to the next reaction without further purification. 1H NMR of the crude product is as follows. 1H NMR (400 MHz, CDCl3) δ 7.78-7.80 (m, 4H), 7.63-7.68 (m, 5H), 7.21-7.28 (m, 6H), 7.12-7.20 (m, 8H), 6.76-6.77 (d, J=7.2 Hz, 1H), 6.59 (s, 1H), 5.52 (s, 2H), 4.03-4.09 (m, 2H), 3.62-3.69 (m, 8H), 2.60-2.62 (m, 2H), 2.42-2.53 (m, 8H), 2.19-2.22 (m 2H), 1.42-1.72 (m, 14H), 1.35-1.40 (m, 10H), and 1.24 (m, 3H).

Workup

  1. filtrationPd—C was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-eadd86ea13ca4bbdbf227d2f87bea8d7
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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