Triethylamine → Methyl 3-{3'-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionate

HRID 1181654Notes

Reaction equation

HRID 1181654 reaction equation
[C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.[CH2:13]([O:15][CH:16]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][NH:35][CH3:36])[CH:29]=2)=[CH:24][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])[CH3:14].C(N(CC)CC)C>ClCCl>[C:8]([O:7][C:1]([CH2:36][NH:35][CH2:34][C:30]1[CH:29]=[C:28]([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][CH:16]([O:15][CH2:13][CH3:14])[C:17]([O:19][CH3:20])=[O:18])=[CH:23][CH:24]=2)[CH:33]=[CH:32][CH:31]=1)=[O:12])([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 68851535Methyl 2-ethoxy-3-(3'-methylaminomethylbiphenyl-4-yl)propionate

Product 1

HCID 68850052Methyl 3-{3'-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.4 g (1.9 mmol) of di-tert-butyl carbonate in 5 ml of dichloromethane is added dropwise to a solution of 0.6 g (1.9 mmol) of methyl 2-ethoxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionate and 0.25 ml (1.9 mmol) of triethylamine in 10 ml of dichloromethane. After stirring at room temperature for 48 hours, the medium is washed with water, extracted with dichloromethane, dried over magnesium sulfate, filtered and evaporated to dryness. The residue obtained is purified by chromatography on a column of silica eluted with a 9/1 heptane/ethyl acetate mixture. 0.78 g of methyl 3-{3′-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionate is obtained in a yield of 85%.

Workup

  1. washthe medium is washed with water
  2. extractionextracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 9/1 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-9b7f6c509aad4001bf4f2a0449d7d4b3
Source dataset
uspto-grants-2007_10
Patent number
US07285568B2

Reaction notes

Loading…