HCID 131710169, compound → HCID 131710168, compound

HRID 1606829Notes

Reaction equation

HRID 1606829 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:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[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:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:41][O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:38])[CH2:28][CH2:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:25])[CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[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 131710169HCID 131710169, compound

Product 1

HCID 131710168HCID 131710168, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 12.5 g. (14 mmoles) of Z-28-31-OtBu in 250 ml. of methanol is hydrogenated for 0.5 hours in the presence of 1.8 g. of palladium-on-carbon. The catalyst is removed by filtration, and the filtrate is evaporated to dryness. The solid residue is triturated with n-hexane, and the mixture is filtered. 10.09 g. (95 %) of H-28-31-OtBu are obtained. M.p.: 130°-140° C, Rf11 = 0.25.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate is evaporated to dryness
  3. customThe solid residue is triturated with n-hexane
  4. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-347d7a8aee2545c5a94ed2c32f63da4d
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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