Triethylamine → (2E)-3-{4-[(2,3-Diphenylpropanoyl)amino]phenyl}-N-hydroxyprop-2-enamide

HRID 1627061Notes

Reaction equation

HRID 1627061 reaction equation
ClC(OCC)=O.C(N(CC)CC)C.[C:14]1([CH:20]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]=[CH:31][C:32](O)=[O:33])=[CH:26][CH:25]=2)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.COC([O:47][NH2:48])(C)C>C1COCC1>[CH:39]1[CH:38]=[CH:37][C:36]([CH2:35][CH:20]([C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27](/[CH:30]=[CH:31]/[C:32]([NH:48][OH:47])=[O:33])=[CH:28][CH:29]=2)=[O:22])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13608208O-(2-Methoxyisopropyl)hydroxylamineHCID 673767133-[4-(2,3-Diphenylpropionylamino)phenyl]-2-propenoic acid

Product 1

HCID 49769465(2E)-3-{4-[(2,3-Diphenylpropanoyl)amino]phenyl}-N-hydroxyprop-2-enamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chloroformate (1.26 mmol, 0.12 mL) and triethylamine (1.37 mmol, 0.19 mL) were added to a cooled (0° C.) solution of 3-[4-(2,3-Diphenylpropionylamino)phenyl]-2-propenoic acid (1.05 mmol, 0.39 g) in dry THF (10 mL), and the mixture was stirred for 10 min. The solid was filtered off, and O-(2-methoxy-2-propyl)hydroxylamine (3.15 mmol, 0.23 mL) was added to the filtrate. The solution was stirred for 15 min at 0° C., then was evaporated under reduced pressure, and the residue was diluted in methanol (10 mL). Amberlyst® 15 ion-exchange resin (105 mg) was added to the solution of the O-protected hydroxamate, and the mixture was stirred at room temperature for 1 h. After, the reaction was filtered and the filtrate was concentrated in vacuo to give the crude MC1895 which was purified by crystallization. 1H NMR (DMSO-d6) δ 3.05 (m, 1H, PhCH2), δ 3.60 (m, 1H, PhCH2), δ 3.75 (m, 1H, PhCHCO), δ 6.36 (d, 1H, PhCH═CHCOOEt), δ 7.15-7.70 (m, 15H, benzene protons and PhCH═CHCOOEt), δ 9.00 (s, 1H, OH), δ 10.23 (s, 1H, CONHPh), δ 10.85 (s, 1H, NHOH). Anal. C, H, N, O.

Workup

  1. filtrationThe solid was filtered off
  2. stirringThe solution was stirred for 15 min at 0° C.
  3. customwas evaporated under reduced pressure
  4. additionthe residue was diluted in methanol (10 mL)
  5. additionAmberlyst® 15 ion-exchange resin (105 mg) was added to the solution of the O-protected hydroxamate
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. filtrationAfter, the reaction was filtered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-521d049ea0c04a6fb524f7dd4ef36d9b
Source dataset
uspto-grants-2014_07
Patent number
US08785493B2

Reaction notes

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