Pyridine → HCID 53729521, compound

HRID 2287900Notes

Reaction equation

HRID 2287900 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:48])[N:17]([CH3:47])[C@@H:18]([C:30](=[O:46])[N:31]([CH3:45])[C@@H:32]([C:40]([NH:42][NH:43][CH3:44])=[O:41])[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:49](OC(=O)C)(=[O:51])[CH3:50].N1C=CC=CC=1>C(Cl)Cl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:48])[N:17]([C@@H:18]([C:30](=[O:46])[N:31]([C@H:32]([CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:40]([NH:42][N:43]([C:49](=[O:51])[CH3:50])[CH3:44])=[O:41])[CH3:45])[CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)[CH3:47])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54194123HCID 54194123, compound

Product 1

HCID 53729521HCID 53729521, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methyl-N-((1R)-1-(N-methyl-N-[(1R)-1-(N'-methylhydrazinocarbonyl)-2-phenylethyl]carbamoyl)-2-(2-naphthyl)ethyl)carbamic acid ((9H-fluoren-9-yl)methyl) ester (0.18 g, 0.28 mmol) in methylene chloride (2 ml) was added acetic acid anhydride (0.053 ml) and pyridine (0.027 ml) and the mixture was stirred overnight. The mixture was concentrated in vacuo and stripped three times with methylene chloride to give 0.21 g (110%) of N-((1R)-1-(N-[(1R)-2-(N'-acetyl-N'-methylhydrazino)-1-benzyl-2-oxoethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamic acid ((9H-fluoren-9-yl)methyl) ester as a colourless oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7d43e9a2431547daa83316ce25370bc9
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

Loading…