Diisopropylethylamine → HCID 59369765, compound

HRID 1807325Notes

Reaction equation

HRID 1807325 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[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](O)=[O:29])[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[NH2:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[C:44]([F:54])[CH:43]=1>C(Cl)Cl>[CH3:49][O:48][C:46](=[O:47])[C:45]1[CH:50]=[C:51]([O:52][CH3:53])[C:42]([NH:41][C:28]([C@H:9]2[C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:31])[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]2)=[O:29])=[CH:43][C:44]=1[F:54]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57955533Methyl 4-amino-2-fluoro-5-methoxybenzoateHCID 59249226(2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxylic acid

Product 1

HCID 59369765HCID 59369765, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 15 mL round-bottomed flask, (2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxylic acid (250 mg, 535 μmol, Eq: 1.00), was combined with CH2Cl2 (3 ml) to give a clear solution. DIPEA (242 mg, 327 μl, 1.87 mmol, Eq: 3.5) and diphenylphosphenic chloride (316 mg, 255 μl, 1.34 mmol, Eq: 2.5) were added and the reaction was stirred at RT for 5 minutes. Methyl 4-amino-2-fluoro-5-methoxybenzoate (107 mg, 535 μmol, Eq: 1.00) was added and the reaction mixture was stirred at RT overnight.

Workup

  1. customto give a clear solution
  2. stirringthe reaction mixture was stirred at RT overnight

Sources & evidence

ORD record
ord-2f232d46df9b46abac21d9c83a0ce2ca
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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