Triethylamine → N-methoxy-N-methyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)acetamide

HRID 1095302Notes

Reaction equation

HRID 1095302 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][O:26][CH2:27][C:28](O)=[O:29])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:32][NH:33][O:34][CH3:35].C(N(CC)CC)C>ClCCl>[CH3:35][O:34][N:33]([CH3:32])[C:28](=[O:29])[CH2:27][O:26][CH2:25][C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 66781548(1-trityl-1H-imidazol-4-ylmethoxy)acetic acid

Product 1

HCID 86632953N-methoxy-N-methyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.03 mmol of (1-trityl-1H-imidazol-4-ylmethoxy)acetic acid and 4.44 mmol of N,O-dimethylhydroxylamine hydrochloride in 100 ml of dichloromethane is mixed with 20.2 mmol of triethylamine and 4.44 mmol of propanephosphonic acid cyclic anhydride [68957-94-8] (50% in ethyl acetate). The reaction mixture is stirred at room temperature for 3 hours and diluted with dichloromethane. The phases are separated and the organic phase is washed with 1M HCl and brine, dried with sodium sulphate and evaporated. The title compound is obtained as a pale yellowish solid from the residue by flash chromatography (SiO2 60 F). Rf=0.45 (dichloromethane-methanol 95:5); Rt=4.11 (gradient I).

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with 1M HCl and brine
  3. dry with materialdried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-84baf8bf054a4dfc930b4c6c23781390
Source dataset
uspto-grants-2012_03
Patent number
US08138176B2

Reaction notes

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