HCID 131710219, compound → HCID 131710218, compound

HRID 1076425Notes

Reaction equation

HRID 1076425 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][CH2:17][C:18]([N:20]1[CH2:58][CH2:57][CH2:56][C@H:21]1[C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:46]([N:48]1[CH2:55][CH2:54][CH2:53][C@H:49]1[C:50]([NH2:52])=[O:51])=[O:47])[C@@H:39]([CH3:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:36])[CH2:26][CH2:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:23])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]>CO.[Pd]>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][CH2:17][C:18]([N:20]1[CH2:58][CH2:57][CH2:56][C@H:21]1[C:22]([NH:24][C@H:25]([C:35]([NH:37][C@H:38]([C:46]([N:48]1[CH2:55][CH2:54][CH2:53][C@H:49]1[C:50]([NH2:52])=[O:51])=[O:47])[C@@H:39]([CH3:45])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:36])[CH2:26][CH2:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:23])=[O:19])=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

4

Reactant 1

HCID 131710219HCID 131710219, compound

Product 1

HCID 131710218HCID 131710218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.95 g of Z-Gly-Phe-Gly-Pro-Glu(OtBu)-Thr(tBu)-Pro-NH2 are dissolved in 80 ml of methanol and the solution is hydrogenated in the presence of 600 mg of palladium charcoal (10 % Pd). After completion of the hydrogenation the catalyst is filtered off, the filtrate is evaporated to a volume of 10 ml, 20 ml of benzene are added, the mixture again concentrated to 10 ml, and the product precipitated with 70 ml of petroleum ether. The smeary precipitate is triturated to give a powder, filtered and dried; yield 3.3 g. On thin layer chromatography on silica gel plates Rf43C = 0.27; Rf52 = 0.24; Rf in chloroform-methanol (8:2) = 0.10.

Workup

  1. filtrationAfter completion of the hydrogenation the catalyst is filtered off
  2. customthe filtrate is evaporated to a volume of 10 ml, 20 ml of benzene
  3. additionare added
  4. concentrationthe mixture again concentrated to 10 ml
  5. customthe product precipitated with 70 ml of petroleum ether
  6. customThe smeary precipitate is triturated
  7. customto give a powder
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-7aa0bbed3a214019ba278f9a2ec6e963
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

Loading…