HCID 178427503, compound → HCID 178427506, compound

HRID 1417886Notes

Reaction equation

HRID 1417886 reaction equation
[NH:1]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@@H:2]([C:6]([N:8]([CH3:41])[C@H:9]([C:27]([NH:29][CH2:30][C:31]([O:33]CC1C=CC=CC=1)=[O:32])=[O:28])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:26])[NH:15][S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])[CH:3]([CH3:5])[CH3:4]>CO>[NH:1]([C:42]([O:44][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:43])[C@@H:2]([C:6]([N:8]([CH3:41])[C@H:9]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:26])[NH:15][S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=1)(=[O:18])=[O:17])=[O:7])[CH:3]([CH3:4])[CH3:5]

Participants

3

Reactant 1

HCID 178427503HCID 178427503, compound

Product 1

HCID 178427506HCID 178427506, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.50 g Boc-D-Val-NMeArg(Tos)-Gly-OBzl (4.44 mmol) dissolved in 80 ml methanol was purged with N2 for 10 min. 1.30 g Pd/C catalyst (10% Fluka lot #273890) was then added, and then H2 was passed directly over the surface of the reaction. TLC showed the reaction to be complete within approximately 0.5 hr. After 1 hr. the catalyst was removed by filtering through a bed of Celite, and the solvent removed at 40° under reduced pressure. The resulting solid was triturated well with 50 ml refluxing ether, filtered, and washed with petroleum ether: yield 3.05 g (78%); TLC Rf(CM) =0.03; Rf(CMA) =0.37; NMR is consistent with structure; FABMS M+H+ =599.45 (expected 599.29).

Workup

  1. customwas purged with N2 for 10 min
  2. addition1.30 g Pd/C catalyst (10% Fluka lot #273890) was then added
  3. customH2 was passed directly over the surface of the reaction
  4. customthe reaction
  5. waitAfter 1 hr
  6. customthe catalyst was removed
  7. filtrationby filtering through a bed of Celite
  8. customthe solvent removed at 40° under reduced pressure
  9. customThe resulting solid was triturated well with 50 ml
  10. temperaturerefluxing ether
  11. filtrationfiltered
  12. washwashed with petroleum ether

Sources & evidence

ORD record
ord-8da9b8c6d29a45fca407fda7b2681712
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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