Triethylamine → N-[3-benzyloxy-4-(2-bromo-acetyl)phenyl]-acetamide

HRID 1433155Notes

Reaction equation

HRID 1433155 reaction equation
C(OP([O-])OCC)C.C(N(CC)CC)C.[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([NH:35][C:36](=[O:38])[CH3:37])[CH:27]=[CH:28][C:29]=1[C:30](=[O:34])[CH:31](Br)[Br:32])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCOC(C)=O>C1COCC1>[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([NH:35][C:36](=[O:38])[CH3:37])[CH:27]=[CH:28][C:29]=1[C:30](=[O:34])[CH2:31][Br:32])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 3780918DiethylphosphiteHCID 85978776N-[3-benzyloxy-4-(2,2-dibromo-acetyl)phenyl]-acetamide

Product 1

HCID 85606679N-[3-benzyloxy-4-(2-bromo-acetyl)phenyl]-acetamideYield 118.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethylphosphite (12.6 μL, 13.5 mg, 97.6 μmol) and triethylamine (13.6 μL, 9.9 mg, 97.6 μmol) in THF (0.1 mL) was added to a stirred solution of N-[3-benzyloxy-4-(2,2-dibromo-acetyl)-phenyl]-acetamide (41 mg, 92.9 μmol) in THF (1.5 mL) at room temperature, and the reaction stirred for 2 hours. The mixture was poured into EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give N-[3-benzyloxy-4-(2-bromo-acetyl)-phenyl]-acetamide (40 mg, >100%), which was seen by NMR to be contaminated with a diethylphosphite-derived contaminant. The material could be used successfully in the following steps without further purification. All analytical data was as reported above.

Workup

  1. washwashed with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e93ff9415bc248818b994272a26f7c21
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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