Triethylamine → HCID 18945259, compound

HRID 399861Notes

Reaction equation

HRID 399861 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(OCC)(=O)C>O>[CH2:32]([O:31][C:29]([N:4]([CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:17]=[CH:18][CH:19]=[CH:20]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2][OH:1])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 18945314HCID 18945314, compound

Product 1

HCID 18945259HCID 18945259, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 3-(2-hydroxyethylaminomethyl)-5-(pyrrol-1-yl)benzoate (0.8 g) and triethylamine (0.48 ml) was added benzyl chloroformate (0.46 ml) under ice cooling. After stirring for 2 hours under ice cooling, the reaction mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with the mixture of chloroform and methanol (15:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-[N-benzyloxycarbonyl-N-(2-hydroxyethyl)aminomethyl]-5-(pyrrol-1-yl)benzoate (1.11 g).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with the mixture of chloroform and methanol (15:1)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0271404008e44083a125e431a83049d9
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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