Triethylamine → 1-[N-(methoxycarbonylmethyl)carbamoyl]-2-[2-(trimethylsilyl)ethoxy]methoxy-4-(3-thienylmethoxy)benzene

HRID 322951Notes

Reaction equation

HRID 322951 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([O:17][CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=2)=[CH:2]1.Cl.[NH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[CH3:32][O:31][C:29]([CH2:28][NH:27][C:12]([C:11]1[CH:15]=[CH:16][C:8]([O:7][CH2:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[CH:9][C:10]=1[O:17][CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:14])=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochlorideHCID 220102164-(3-Thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoic acid

Product 1

HCID 220102001-[N-(methoxycarbonylmethyl)carbamoyl]-2-[2-(trimethylsilyl)ethoxy]methoxy-4-(3-thienylmethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-thienylmethoxy)-2-[2-(trimethylsilyl)ethoxy]methoxybenzoic acid (3.09 g), methyl aminoacetate hydrochloride (0.99 g), 1-hydroxybenzotriazole (1.28 g), triethylamine (0.8 g) and dimethylformamide (50 mL) is stirred at ambient temperature for 16 hours. It is then concentrated in vacuo and the resulting residue is dissolved in ethyl acetate (100 mL), washed quickly with hydrochloric acid (2×50 mL; 1 N), and then washed with saturated aqueous sodium bicarbonate solution (50 mL) and with water (50 mL), then dried over magnesium sulphate, filtered and concentrated in vacuo, to give 1-[N-(methoxycarbonylmethyl)carbamoyl]-4-(3-thienylmethoxy)-2-[2-(trimethylsilyl)ethoxy]methoxybenzene, in the form of a yellow oil.

Workup

  1. concentrationIt is then concentrated in vacuo
  2. dissolutionthe resulting residue is dissolved in ethyl acetate (100 mL)
  3. washwashed quickly with hydrochloric acid (2×50 mL; 1 N)
  4. washwashed with saturated aqueous sodium bicarbonate solution (50 mL) and with water (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35d35a47248f438d871f46631891dc44
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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