Methyl chloroformate → (3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

HRID 1969022Notes

Reaction equation

HRID 1969022 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=1.Cl[C:30]([O:32][CH3:33])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:6]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformate2×HCID 8471Triethylamine2×HCID 58288498{3-[2-(Benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester

Product 1

HCID 58288472(3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To {3-[2-(benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester (0.076, 0.17 mmol) and methyl chloroformate (0.01 mL, 0.18 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.02 mL, 0.18 mmol), and the reaction was stirred at room temperature for 3 hours. Some starting material was still observed by analytical LCMS, so additional methyl chloroformate (0.02 mL) and triethylamine (0.03 mL) was added, and the reaction was stirred overnight. The mixture was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred overnight
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-537e0e6ff668484faa58e66c9bccbedc
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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