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

HRID 1360137Notes

Reaction equation

HRID 1360137 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 60F). 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-0c66118770eb4c99a0a7651d1994ac64
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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