Dimethyl Sulfide → 6-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-2-naphthoic acid

HRID 1807244Notes

Reaction equation

HRID 1807244 reaction equation
[Cl:1][C:2]1[C:3]([F:45])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[CH:37]=[C:36]([C:41]([O:43]C)=[O:42])[CH:35]=[CH:34]3)=[O:29])[CH:5]=[CH:6][CH:7]=1.[Br-].[Al+3].[Br-].[Br-].CSC>C(Cl)Cl>[Cl:1][C:2]1[C:3]([F:45])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[CH:37]=[C:36]([C:41]([OH:43])=[O:42])[CH:35]=[CH:34]3)=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 166749BromhydrolHCID 59249441Methyl 6-((2r,3s,4r,5s)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-2-naphthoate

Product 1

HCID 592496776-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-2-naphthoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 6-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-2-naphthoate (120 mg, 0.184 mmol) in methylene chloride 10 ml), aluminum bromide (295 mg, 1.11 mmol) and dimethyl sulfide (150 ul, 2.03 mmol) were added and the mixture was stirred at rt for overnight. LC/mass indicates complete reaction.

Workup

  1. customreaction

Sources & evidence

ORD record
ord-deba92dd6df848f582e97c975eb54418
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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