Ammonium Acetate → (S)-(9H-fluoren-9-yl)methyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-methylpyrrolidine-1-carboxylate

HRID 588952Notes

Reaction equation

HRID 588952 reaction equation
C([O-])(=O)C.[NH4+:5].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][NH:15][C:16]([C@:18]2([CH3:40])[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][CH2:26][CH:27]2[C:39]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=O)=[CH:9][CH:8]=1>C1(C)C(C)=CC=CC=1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[NH:5][C:16]([C@:18]3([CH3:40])[CH2:22][CH2:21][CH2:20][N:19]3[C:23]([O:25][CH2:26][CH:27]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]4[C:39]3=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:24])=[N:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 59668673HCID 59668673, compound

Product 1

HCID 67460873(S)-(9H-fluoren-9-yl)methyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-methylpyrrolidine-1-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of ammonium acetate (844 mg; 10.97 mmol) and (S)-(9H-fluoren-9-yl)methyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-2-methylpyrrolidine-1-carboxylate (intermediate LS31; 1.00 g; 1.83 mmol) was heated to 140° C. in 25 mL xylene for 2.5 h at which time the reaction mixture was concentrated and loaded with dichloromethane onto a Biotage 40 samplet. Purification via Biotage (5 to 60% ethyl acetate/hexane over 1000 mL with 400 mL hold time) provided (S)-(9H-fluoren-9-yl)methyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-methylpyrrolidine-1-carboxylate (intermediate LS32; 469 mg; 49%) as an amber liquid. LC (Cond'n 12): RT=3.09 min; MS: Anal. Calcd. for [M+H]+ C29H26BrN3O2: 528.1. found 528.5.

Workup

  1. concentrationwas concentrated and loaded with dichloromethane onto a Biotage 40 samplet
  2. customPurification via Biotage (5 to 60% ethyl acetate/hexane over 1000 mL with 400 mL hold time)

Sources & evidence

ORD record
ord-059817ee1a30452fb3a5932d85513fb1
Source dataset
uspto-grants-2016_01
Patent number
US09227961B2

Reaction notes

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