Pyridinium chloride → HCID 178448275, compound

HRID 847321Notes

Reaction equation

HRID 847321 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:27]([NH:29][C@@H:30]([CH2:54][CH:55]1[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]1)[C@@H:31]([OH:53])[CH2:32][C@@H:33]([CH:50]([CH3:52])[CH3:51])[CH2:34][CH2:35][NH:36][C:37]([NH:39]C(=O)OCC1C=CC=CC=1)=[NH:38])=[O:28])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:61].N1C=CC=CC=1>CO.[Pd]>[ClH:61].[CH:55]1([CH2:54][C@H:30]([NH:29][C:27]([C@@H:20]([NH:19][C:17]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:18])[CH2:21][C:22]2[N:26]=[CH:25][NH:24][CH:23]=2)=[O:28])[C@@H:31]([OH:53])[CH2:32][C@@H:33]([CH:50]([CH3:52])[CH3:51])[CH2:34][CH2:35][NH:36][C:37]([NH2:39])=[NH:38])[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]1

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 178448276HCID 178448276, compound

Product 1

HCID 178448275HCID 178448275, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.110 g (0.132 mmol) of benzyl [N-[(3S,5S,6S)-6-[[N-[N-(t-butoxycarbonyl)-3-phenyl-L-alanyl]-L-histidyl]amino]-7-cyclohexyl-5-hydroxy-3-isopropylheptyl]amidino]carbamate and 0.015 mg (0.132 mmol) of pyridine hydrochloride are dissolved in 2.4 ml of methanol and hydrogenated in the presence of 20 mg of palladium on charcoal (5%) for 3 hours at room temperature and atmospheric pressure. After completion of the hydrogen uptake the catalyst is filtered off and the filtrate is evaporated under reduced pressure. In this manner there is obtained 0.074 g of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-6-guanidino-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate hydrochloride as an amorphous solid, MS: 697 (M+H)+.

Workup

  1. filtrationAfter completion of the hydrogen uptake the catalyst is filtered off
  2. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-15860730490c4e02acc13c2bc434725c
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

Loading…