Ethanol → 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-benzoic acid ethyl ester

HRID 554586Notes

Reaction equation

HRID 554586 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=2)=[C:12]([CH2:26][N:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:28][CH3:29])[CH:11]=1)[C:2]1C=CC=CC=1.S(=O)(=O)(O)O.[CH3:46][CH2:47]O>>[CH2:1]([O:8][C:9](=[O:40])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([CH2:22][C:23]([O:25][CH2:46][CH3:47])=[O:24])[CH:21]=2)=[C:12]([CH2:26][N:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:28][CH3:29])[CH:11]=1)[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 585650203-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid benzyl ester

Product 1

HCID 585652203-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-benzoic acid ethyl ester

Conditions

Temperature
95 °C

Procedure

3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid benzyl ester (1.74 g, 3.2 mmol) in EtOH (200 mL) was treated with sulfuric acid (2 mL), and the reaction was stirred at 95° C. for 2 hours. The mixture was cooled to room temperature and concentrated, and the residue was partitioned between EtOAc and H2O. The solution was extracted with EtOAc, and the combined organic layers were washed with 1N aqueous HCl and concentrated. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-benzoic acid ethyl ester.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customthe residue was partitioned between EtOAc and H2O
  4. extractionThe solution was extracted with EtOAc
  5. washthe combined organic layers were washed with 1N aqueous HCl
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d6bb91ec556e4bd586f60a4c496477bb
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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