HCID 178418361, compound → HCID 178462341, compound

HRID 1249017Notes

Reaction equation

HRID 1249017 reaction equation
[NH:1]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[C@H:2]([C:14]([NH:16][C@H:17]([C:28]([NH:30][C@H:31]([C:43]([N:45]1[CH2:73][CH2:72][CH2:71][C@H:46]1[C:47]([NH:49][C@H:50]([C:61]([O:63]CC1C=CC=CC=1)=[O:62])[CH2:51][CH2:52][CH2:53][NH:54][C:55](=[NH:60])[NH:56][N+]([O-])=O)=[O:48])=[O:44])[CH2:32][C:33](=[O:42])[O:34]CC1C=CC=CC=1)=[O:29])[C@@H:18]([CH3:27])[O:19]CC1C=CC=CC=1)=[O:15])[CH2:3][C:4](=[O:13])[O:5]CC1C=CC=CC=1.[H][H]>C(O)(=O)C.O.CO.[Pd]>[NH:1]([C:74]([O:76][C:77]([CH3:78])([CH3:80])[CH3:79])=[O:75])[C@H:2]([C:14]([NH:16][C@H:17]([C:28]([NH:30][C@H:31]([C:43]([N:45]1[CH2:73][CH2:72][CH2:71][C@H:46]1[C:47]([NH:49][C@H:50]([C:61]([OH:63])=[O:62])[CH2:51][CH2:52][CH2:53][NH:54][C:55](=[NH:56])[NH2:60])=[O:48])=[O:44])[CH2:32][C:33](=[O:34])[OH:42])=[O:29])[C@@H:18]([CH3:27])[OH:19])=[O:15])[CH2:3][C:4](=[O:5])[OH:13]

Participants

7

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178462264HCID 178462264, compound

Product 1

HCID 178462341HCID 178462341, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

BOC-Asp(OBzl)-Thr(Bzl)-Asp(OBzl)-Pro-Arg(NO2)-OBzl, was dissolved in a mixture of acetic acid (500 ml), water (500 ml), and methanol (3-5 liters). Palladium 10% on activated carbon (100-200 g) was added to the solution and hydrogen gas passed through the mixture for 20-40 hours. The catalyst was removed by filtration and the filtrate evaporated to dryness. The residue was triturated with ether (3-4 liters), and the resulting solid filtered to produce BOC-Asp-Thr-Asp-Pro-Arg. The yield was about 40-60%.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated to dryness
  3. customThe residue was triturated with ether (3-4 liters)
  4. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-51cda3f93ec74451b9761eb2392fb0d7
Source dataset
uspto-grants-1986_12
Patent number
US04628045

Reaction notes

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