HCID 86664858, compound → HCID 86664857, compound

HRID 1952540Notes

Reaction equation

HRID 1952540 reaction equation
[CH2:1]([N:8]1[C:12]([C:13](=[O:74])[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][CH2:45][N:46]3[C:54](=[O:55])[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:47]3=[O:56])=[C:17]([CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][N:63]3[C:71](=[O:72])[C:70]4[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=4)[C:64]3=[O:73])[CH:16]=2)=[CH:11][C:10]([CH:75]=[CH:76][C:77]([O:79][CH2:80][CH3:81])=[O:78])=[C:9]1[C:82]#[C:83][C:84]([OH:97])([C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)[C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O>[CH2:1]([N:8]1[C:12]([C:13](=[O:74])[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][CH2:45][N:46]3[C:54](=[O:55])[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:47]3=[O:56])=[C:17]([CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][N:63]3[C:71](=[O:72])[C:70]4[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=4)[C:64]3=[O:73])[CH:16]=2)=[CH:11][C:10]([CH2:75][CH2:76][C:77]([O:79][CH2:80][CH3:81])=[O:78])=[C:9]1[C:82]#[C:83][C:84]([OH:97])([C:91]1[CH:92]=[CH:93][CH:94]=[CH:95][CH:96]=1)[C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86664858HCID 86664858, compound

Product 1

HCID 86664857HCID 86664857, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 9 (0.07 g, 0.06 mmol) in EtOAc (20 mL) was added dry powdered 10% Pd—C (0.007 g). The resulting mixture was stirred at room temperature for 48 hours under H2 balloon. Pd—C was filtered off and the filtrate was concentrated to give 10 as colorless oil (0.07 g, 80%). The crude product was subjected to the next reaction without further purification. 1H NMR (CDCl3) δ 7.78-7.80 (m, 6H), 7.65-7.69 (m, 7H), 7.14-7.33 (m, 14H), 6.76 (d, J=7.2 Hz, 1H), 6.61 (s, 1H), 5.52 (s, 2H), 4.05 (q, J=6.8 Hz, 2H), 3.62-3.67 (m, 8H), 2.62 (m, 2H), 2.45-2.54 (m, 8H), 2.19-2.22 (m, 2H), 1.56-1.67 (m, 12H), and 1.22-1.35 (m, 17H),

Workup

  1. dry with materialdry powdered 10% Pd—C (0.007 g)
  2. filtrationPd—C was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-80a094ace34347e6b0092eb0d26efe32
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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