HCID 131710179, compound → HCID 131710178, compound

HRID 1606837Notes

Reaction equation

HRID 1606837 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]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[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].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:48]([NH:50][C@H:51]([C:53]([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[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]([CH3:25])([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

4

Reactant 1

HCID 131710179HCID 131710179, compound

Product 1

HCID 131710178HCID 131710178, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.1 g. (6.2 mmoles) of Z-27-32-OtBu in 120 ml. of methanol is hydrogenated in the presence of 1 g. of palladium-on-carbon. When the reaction terminates, the catalyst is filtered off, and the filtrate is evaporated to dryness. The residue is crystallized from a mixture of ethanol and ether. 4.35 g. (83 %) of H-27-32-OtBu are obtained. M.p.: 192°-194°C; Rf12 = 0.25; Rf3 = 0.1.

Workup

  1. customWhen the reaction terminates
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated to dryness
  4. customThe residue is crystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-71d6380d209949118f27a2a22c726289
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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