HCID 131710177, compound → HCID 131710176, compound

HRID 1606836Notes

Reaction equation

HRID 1606836 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:24]([NH:26][C@H:27]([C:37]([NH:39][C@H:40]([C:43]([NH:45][C@H:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH3:47])=[O:44])[CH2:41][OH:42])=[O:38])[CH2:28][CH2:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:25])[CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>[Pd].CO>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:24]([NH:26][C@H:27]([C:37]([NH:39][C@H:40]([C:43]([NH:45][C@H:46]([C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])[CH3:47])=[O:44])[CH2:41][OH:42])=[O:38])[CH2:28][CH2:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:25])[CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 1

HCID 131710177HCID 131710177, compound

Product 1

HCID 131710176HCID 131710176, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 8.0 g. (8.8 mmoles) of Z-28-32-OtBu in 160 ml. of methanol is hydrogenated in the presence of 1 g. of palladium-on-carbon. When the reaction terminates, the catalyst is filtered off, the filtrate is evaporated to dryness, and the residue is triturated with ether and petroleum ether. 6.4 g. (94 %) of H-28-32-OtBu are obtained. M.p.: 138-139°C; Rf12 = 0.1; [α]D = -9.7° (c = 1, in ethanol).

Workup

  1. customWhen the reaction terminates
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated to dryness
  4. customthe residue is triturated with ether and petroleum ether

Sources & evidence

ORD record
ord-563f682aac934cc98333a4382ba95a56
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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