Ammonium formate → HCID 10745775, compound

HRID 1759762Notes

Reaction equation

HRID 1759762 reaction equation
[NH:1]([C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])=[O:4].C([O-])=O.[NH4+]>[Pd].CN(C=O)C>[NH:1]([C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10628222HCID 10628222, compound

Product 1

HCID 10745775HCID 10745775, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Trt-Gly-Gly-Phe-Gly-OBzl (670 mg), 10% Pd-C (100 mg), and ammonium formate (200 mg) were added to DMF (5 ml) and stirred for three hours. The reaction mixture was filtered, the filtrate was evaporated to dryness under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=8:1 solution) to obtain the title compound (300 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=8:1 solution)

Sources & evidence

ORD record
ord-b4623e47d6e1483c839be9ec48a5e375
Source dataset
uspto-grants-2005_01
Patent number
US06838450B2

Reaction notes

Loading…