HCID 131710180, compound → HCID 131710181, compound

HRID 1606839Notes

Reaction equation

HRID 1606839 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:29]([NH:31][C@H:32]([C:41]([NH:43][C@H:44]([C:54]([NH:56][C@H:57]([C:60]([NH:62][C@H:63]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH3:64])=[O:61])[CH2:58][OH:59])=[O:55])[CH2:45][CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:42])[CH2:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:30])[CH2:20][CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:17])[CH3:15])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]>[Pd].CO>[NH2:1][C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:29]([NH:31][C@H:32]([C:41]([NH:43][C@H:44]([C:54]([NH:56][C@H:57]([C:60]([NH:62][C@H:63]([C:65]([O:67][C:68]([CH3:69])([CH3:70])[CH3:71])=[O:66])[CH3:64])=[O:61])[CH2:58][OH:59])=[O:55])[CH2:45][CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:42])[CH2:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:30])[CH2:20][CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:17])[CH3:15])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

4

Reactant 1

HCID 131710180HCID 131710180, compound

Product 1

HCID 131710181HCID 131710181, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.0 g. (3.48 mmoles) of Z-25-32-OtBu in 140 ml. of methanol is hydrogenated in the presence of 0.5 g. of palladium-on-carbon. When the reaction terminates, the catalyst is filtered off; the filtrate is evaporated to dryness; the residue is triturated with ether and filtered off. 3.4 g. (96 %) of H-25-32-OtBu are obtained. M.p.: 188°-190°C; Rf4 = 0.5; [α]D = -6.6° (c = 0.89, in DMF).

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
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-a6c7c0f4b6874887855b7528c392c16a
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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