Benzyloxycarbonyl-prolyl-histidyl-leucine, tert-Butyl Ester → HCID 178445971, compound

HRID 1855751Notes

Reaction equation

HRID 1855751 reaction equation
C(OC([N:11]1[CH2:40][CH2:39][CH2:38][C@H:12]1[C:13]([NH:15][C@H:16]([C:23]([NH:25][C@H:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1)=[O:14])=O)C1C=CC=CC=1>[Pd].C(O)(=O)C>[NH:11]1[CH2:40][CH2:39][CH2:38][C@H:12]1[C:13]([NH:15][C@H:16]([C:23]([NH:25][C@H:26]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1)=[O:14]

Participants

4

Reactant 1

HCID 178445970Benzyloxycarbonyl-prolyl-histidyl-leucine, tert-Butyl Ester

Product 1

HCID 178445971HCID 178445971, compoundYield 116.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the protected tripeptide of formula III, Z-Pro-His-Leu-OBut (5.9 g, 10.6 mmol, described in Example 2), and 5% palladium on carbon (600 mg) in glacial acetic acid is subjected to hydrogenation. The mixture is filtered and the filtrate evaporated under reduced pressure to give 5.2 g of H-Pro-His-Leu-OBut in the form of its acetate salt. This product is suspended in toluene and the toluene then is removed by distillation so the excess acetic acid is removed azeotropically.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-982213a31ea14dedb9d257f46a607fca
Source dataset
uspto-grants-1980_08
Patent number
US04216209

Reaction notes

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