Pyridine → Benzyl 2-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 415248Notes

Reaction equation

HRID 415248 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8]C)=[O:6].N1C=CC=CC=1.Cl[C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[O:22]>ClCCl>[OH:13][C:3]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:10][CH:11]=[CH:12][C:2]=1[NH:1][C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 98601531-Pyrrolidinecarboxylic acid, 2-(chlorocarbonyl)-, phenylmethyl esterHCID 22096614Ethyl 3-amino-2-hydroxybenzoate

Product 1

HCID 66621344Benzyl 2-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of ethyl 3-amino-2-hydroxybenzoate (0.601 g, 3.6 mmol) and pyridine (0.633 g, 8 mmol) in anhydrous dichloromethane (20 mL) was added dropwise a solution of benzyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate (1.12 g, 4 mmol) in anhydrous dichloromethane (5 mL). After the addition, the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane, washed with water (30 mL×3), 1N hydrochloric acid (30 mL×3), brine (30 mL), dried over anhydrous sodium sulfate, and concentrated to give benzyl 2-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylate (1.43 g). LC-MS (ESI) m/z: 399 (M+1)+.

Workup

  1. additionAfter the addition
  2. washwashed with water (30 mL×3), 1N hydrochloric acid (30 mL×3), brine (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-15cbb0fab20540eca88653384ff8d73c
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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