HCID 54161281, compound → HCID 54517706, compound

HRID 2083835Notes

Reaction equation

HRID 2083835 reaction equation
[CH3:1][O:2][C:3](=[O:60])[C@H:4]([CH2:56][CH:57]([CH3:59])[CH3:58])[NH:5][C:6](=[O:55])[C@@H:7]([CH2:51][C:52](=[O:54])[NH2:53])[NH:8][C:9](=[O:50])[C@H:10]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1)[NH:11][C:12](=[O:41])[C@H:13]([CH2:39][OH:40])[NH:14][C:15](=[O:38])[C@H:16]([CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH:17]C(OCC1C=CC=CC=1)=O.[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:60])[C@H:4]([CH2:56][CH:57]([CH3:58])[CH3:59])[NH:5][C:6](=[O:55])[C@@H:7]([CH2:51][C:52](=[O:54])[NH2:53])[NH:8][C:9](=[O:50])[C@H:10]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1)[NH:11][C:12](=[O:41])[C@H:13]([CH2:39][OH:40])[NH:14][C:15](=[O:38])[C@H:16]([CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH2:17]

Participants

5

Reactant 2

HCID 54161281HCID 54161281, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54517706HCID 54517706, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Nα -Benzyloxycarbonyl-L-tryptophyl-L-seryl-L-tyrosyl-D-asparaginyl-L-leucine methyl ester, 3.75 g. is dissolved in 200 ml. of absolute methanol, 375 mg. of 20% palladium-on-carbon added and the material reduced with hydrogen during 50 minutes. The catalyst is removed by filtration and the filtrate evaporated under reduced pressure; 1.83 g. The catalyst is extracted with 400 ml. of boiling methanol, separated by filtration and the filtrate evaporated to yield 1.22 g. of additional product.

Workup

  1. dissolutionis dissolved in 200 ml
  2. customThe catalyst is removed by filtration
  3. customthe filtrate evaporated under reduced pressure
  4. extractionThe catalyst is extracted with 400 ml
  5. customof boiling methanol, separated by filtration
  6. customthe filtrate evaporated
  7. customto yield 1.22 g

Sources & evidence

ORD record
ord-2460fbf867534772aecdeea8353c2297
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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