HCID 131710189, compound → HCID 131710188, compound

HRID 1606843Notes

Reaction equation

HRID 1606843 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C:17]([NH:19][C@H:20]([C:29]([NH:31][C@H:32]([C:42]([NH:44][C@H:45]([C:48]([NH:50][C@H:51]([C:53]([NH:55][C@H:56]([C:66]([NH:68][C@H:69]([C:71]([NH:73][C@H:74]([C:82]([N:84]1[CH2:127][CH2:126][CH2:125][C@H:85]1[C:86]([NH:88][C@H:89]([C:94]([NH:96][C@H:97]([C:107]([NH:109][C@H:110]([C:118]([O:120][C:121]([CH3:124])([CH3:123])[CH3:122])=[O:119])[CH2:111][C:112]1[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=1)=[O:108])[CH2:98][CH2:99][C:100](=[O:106])[O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:95])[CH2:90][CH:91]([CH3:93])[CH3:92])=[O:87])=[O:83])[CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)=[O:72])[CH3:70])=[O:67])[CH2:57][CH2:58][C:59](=[O:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:54])[CH3:52])=[O:49])[CH2:46][OH:47])=[O:43])[CH2:33][CH2:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:30])[CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:18])[CH2:8][CH2:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:5])[CH3:3]>[Pd].CN(C=O)C>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:17]([NH:19][C@H:20]([C:29]([NH:31][C@H:32]([C:42]([NH:44][C@H:45]([C:48]([NH:50][C@H:51]([C:53]([NH:55][C@H:56]([C:66]([NH:68][C@H:69]([C:71]([NH:73][C@H:74]([C:82]([N:84]1[CH2:127][CH2:126][CH2:125][C@H:85]1[C:86]([NH:88][C@H:89]([C:94]([NH:96][C@H:97]([C:107]([NH:109][C@H:110]([C:118]([O:120][C:121]([CH3:122])([CH3:123])[CH3:124])=[O:119])[CH2:111][C:112]1[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=1)=[O:108])[CH2:98][CH2:99][C:100](=[O:106])[O:101][C:102]([CH3:103])([CH3:104])[CH3:105])=[O:95])[CH2:90][CH:91]([CH3:93])[CH3:92])=[O:87])=[O:83])[CH2:75][C:76]1[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=1)=[O:72])[CH3:70])=[O:67])[CH2:57][CH2:58][C:59](=[O:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:54])[CH3:52])=[O:49])[CH2:46][OH:47])=[O:43])[CH2:33][CH2:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:30])[CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:18])[CH2:8][CH2:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:5])[CH3:3]

Participants

4

Reactant 1

HCID 131710189HCID 131710189, compound

Product 1

HCID 131710188HCID 131710188, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

8.5 g. 4.41 mmoles) of Z-27-39-OtBu are dissolved in 850 ml. of dry DMF, and the mixture is hydrogenated in the presence of palladium-on-carbon. At the end of the reaction, the catalyst is removed by filtration; the filtate is evaporated to dryness, and the residue is triturated with ether. 7.65 g. (96.9 %) of H-27-39-OtBu are obtained. M.p.: 197°C (under decomposition), Rf12 = 0.3.

Workup

  1. customAt the end of the reaction
  2. customthe catalyst is removed by filtration
  3. customthe filtate is evaporated to dryness
  4. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-da7945e219f34f1bb6652e1167f69852
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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