Chlorosuccinimide → HCID 178495699, compound

HRID 1524254Notes

Reaction equation

HRID 1524254 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@:6]([C:12]([N:14]1[C@@H:18]([CH3:19])[CH2:17][CH2:16][C@H:15]1[C:20]1[NH:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[NH:41][C:40]([C@@H:42]5[CH2:46][C@H:45]([CH2:47][O:48][CH3:49])[CH2:44][N:43]5[C:50](=[O:61])[C@@H:51]([NH:56][C:57](=[O:60])[O:58][CH3:59])[C@H:52]([O:54][CH3:55])[CH3:53])=[N:39][CH:38]=4)=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)=[CH:23][N:24]=1)=[O:13])([C@@H:8]([CH3:11])[O:9][CH3:10])[NH2:7])=[O:4].[Cl:62]N1C(=O)CCC1=O>CN(C=O)C>[Cl:62][C:38]1[N:39]=[C:40]([C@@H:42]2[CH2:46][C@H:45]([CH2:47][O:48][CH3:49])[CH2:44][N:43]2[C:50](=[O:61])[C@@H:51]([NH:56][C:57](=[O:60])[O:58][CH3:59])[C@H:52]([O:54][CH3:55])[CH3:53])[NH:41][C:37]=1[C:34]1[CH:35]=[CH:36][C:31]([C:28]2[CH:27]=[CH:26][C:25]([C:22]3[NH:21][C:20]([C@@H:15]4[CH2:16][CH2:17][C@H:18]([CH3:19])[N:14]4[C:12](=[O:13])[C@@:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])([C@@H:8]([CH3:11])[O:9][CH3:10])[NH2:7])=[N:24][CH:23]=3)=[CH:30][CH:29]=2)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86702343HCID 86702343, compound

Product 1

HCID 178495699HCID 178495699, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of methyl {(2S,3R)-1-((2S,4S)-2-(5-(4′-(2-((2S,5S)-1-((2S,3R)-2-(methoxycarbonylamino)-O-methyl-L-threonyl)-5-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-yl}carbamate (0.12 g, 0.15 mmol) in DMF (1.5 mL) was added N-chlorosuccinimide (0.05 g, 0.38 mmol). The resulting solution was heated to 45° C. for 3 h and cooled to room temperature. The reaction solution was purified by preparative HPLC (Gemini C18, 20-75% MeCN/H2O (0.1% TFA)). The desired fractions were combined and lyophilized to provide methyl {(2S,3R)-1-((2S,4S)-2-(4-chloro-5-(4′-(2-((2S,5S)-1-((2S,3R)-2-(methoxycarbonylamino)-O-methyl-L-threonyl)-5-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-yl}carbamate (0.006 g, 5%).

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction solution was purified by preparative HPLC (Gemini C18, 20-75% MeCN/H2O (0.1% TFA))

Sources & evidence

ORD record
ord-6bb05fb7078147d08b7497fcd30aecac
Source dataset
uspto-grants-2015_07
Patent number
US09079887B2

Reaction notes

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