Diisopropylethylamine → HCID 51357808, compound

HRID 909100Notes

Reaction equation

HRID 909100 reaction equation
[Cl:1][C:2]1[C:3]([F:28])=[C:4]([CH: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])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][NH:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl[S:39]([C:42]1[CH:50]=[CH:49][C:45]([C:46]([OH:48])=[O:47])=[CH:44][CH:43]=1)(=[O:41])=[O:40]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:28])=[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]([CH3:25])([CH3:27])[CH3:26])[CH2:10][N:9]2[S:39]([C:42]2[CH:43]=[CH:44][C:45]([C:46]([OH:48])=[O:47])=[CH:49][CH:50]=2)(=[O:41])=[O:40])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 67095372rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile

Product 1

HCID 51357808HCID 51357808, compoundYield 385%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (80 mg, 0.0189 mmol) and diisopropylethylamine (122 mg, 0.942 mmol) in CH2Cl2 (6 mL) was added p-(chlorosulfonyl)benzoic acid (70.0 mg, 0.283 mmol, Eastman) and the reaction mixture was stirred at room temp. for 6 hrs. The resulting mixture was diluted with EtOAc, washed with aqueous Na2CO3, 1N HCl and brine, and concentrated to dryness to give rac-4-[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-sulfonyl]-benzoic acid (44.2 mg, 38%) as a white solid. HRMS (ES+) m/z Calcd for C29H26Cl2F2N2O4S H [(M+H)+]: 607.1031; Found: 607.1032.

Workup

  1. washwashed with aqueous Na2CO3, 1N HCl and brine
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-db06e0726f8740c9920669cc4a1ae61b
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

Loading…