HCID 131710170, compound → HCID 131710171, compound

HRID 1606831Notes

Reaction equation

HRID 1606831 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:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:46][O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[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].[H][H]>[Pd].CO>[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:52]([O:54][C:55]([CH3:56])([CH3:58])[CH3:57])=[O:53])[CH2:46][O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:43])[CH2:33][CH2:34][C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:30])[CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:18])[CH2:8][CH2:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:5])[CH3:3]

Participants

5

Reactant 2

HCID 131710170HCID 131710170, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131710171HCID 131710171, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.61 g. (6.85 mmoles) of Z-27-31-OtBu are dissolved in 150 ml. of methanol with gentle heating. The solution is cooled to room temperature; 1 g. of palladium-on-carbon is added to it, and gaseous hydrogen is bubbled into the mixture for 0.5 hours. The catalyst is removed by filtration, the filtrate is evaporated to dryness, the solid residue is triturated with n-hexane; and the mixture is filtered. 5.55 g. (97.6 %) of H-27-31-OtBu are obtained. M.p.: 138°-142° C, Rf2 = 0.15.

Workup

  1. customis bubbled into the mixture for 0.5 hours
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated to dryness
  4. customthe solid residue is triturated with n-hexane
  5. filtrationand the mixture is filtered

Sources & evidence

ORD record
ord-0a5826a3eaa34b1da09b3ba26ca5c91e
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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