Diisopropylethylamine → tert-Butyl (3-{[3-(3-nitrophenyl)propanoyl]amino}phenyl)carbamate

HRID 541950Notes

Reaction equation

HRID 541950 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([OH:14])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:15][C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([NH:15][C:16]2[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH:19]=[CH:20][CH:21]=2)=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27602243-(3-Nitrophenyl)propionic acidHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 57962418tert-Butyl (3-{[3-(3-nitrophenyl)propanoyl]amino}phenyl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(3-nitrophenyl)propanoic acid (0.43 g, 2.2 mmol) and tert-butyl (3-aminophenyl)carbamate (0.50 g, 2.4 mmol) in acetonitrile (16 mL) was treated with O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.2 g, 3.3 mmol) followed by N,N-diisopropylethylamine (0.57 mL, 3.3 mmol) and stirred for 16 h. The reaction mixture was concentrated and diluted with brine (80 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a crude residue. This material was purified by flash column chromatography to give the desired product (0.87 g, 98%) as an off-white foam. LCMS for C16H16N3O5 ([M-(t-Bu)+H]+H)+: m/z=330.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with brine (80 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-19aa25fcff2540548efd0b0206673fbb
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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