Diisopropylethylamine → tert-Butyl (1S)-1-(3-bromo-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)amino]ethylcarbamate

HRID 724723Notes

Reaction equation

HRID 724723 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[I:8].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:50][CH2:51][C:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:53].C(N(CC)C(C)C)(C)C>C(=O)(O)[O-].[Na+].CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[I:8])[CH2:9][C@H:10]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11](=[O:13])[NH:50][CH2:51][C:52](=[O:53])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 69597598(2S)-3-(3-bromo-4-iodophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

Product 1

HCID 58746572tert-Butyl (1S)-1-(3-bromo-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)amino]ethylcarbamateYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of (2S)-3-(3-bromo-4-iodophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (4.10 g, 6.10 mmol), N,N-dimethylformamide (49 mL) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.24 g, 9.59 mmol) was stirred at 25° C. After stirring for 10 min, added 2-amino-1-phenylethanone hydrochloride (2.24 g, 13.1 mmol) and N,N-diisopropylethylamine (7.60 mL). The reaction was stirred at 25° C. for 2 h. The reaction was diluted with saturated sodium bicarbonate and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.2 g, 33%). MF=C22H24BrIN2O4; LCMS found for C22H25BrIN2O4 (M+H−Boc)+: m/z=487.

Workup

  1. stirringThe reaction was stirred at 25° C. for 2 h
  2. extractionextracted with ethyl acetate three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f4f35f990acf460e80d8137118181220
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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