Pyrrole-2-Carboxylic Acid → (Pyrrole-2-carbonyl)-N-(benzyl)glycine-t-butyl ester

HRID 2393253Notes

Reaction equation

HRID 2393253 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CCN(C(C)C)C(C)C.[C:33]([O:37][C:38](=[O:48])[CH2:39][NH:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:36])([CH3:35])[CH3:34]>ClCCl.C(OCC)(=O)C>[C:33]([O:37][C:38](=[O:48])[CH2:39][N:40]([C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 12473Pyrrole-2-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 11020442Tert-butyl 2-(benzylamino)acetate

Product 1

HCID 70020108(Pyrrole-2-carbonyl)-N-(benzyl)glycine-t-butyl esterYield 34.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension containing 3.00 g (27.0 mmol) of pyrrole-2-carboxylic acid in 75 mL of anhydrous dichloromethane under a nitrogen atmosphere at 0° C. was added 6.96 g (27.0 mmol of BOPCl and 14.1 mL (81.0 mmol) of DIEA. After stirring for 30 minutes, 5.97 g (27.0 mmol) of N-(benzyl)glycine-t-butyl ester was added and the reaction allowed to warn to room temperature overnight. The reaction was diluted with ethyl acetate and washed with a 5% potassium hydrogensulfate, saturated sodium bicarbonate solution and brine. The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient of 100% hexane to (60% hexane/ethyl acetate to afford 2.92 g (34.4%) of the title compound is a white solid. FAB MS [M+H] m/z Calcd: 315, Found: 315.

Workup

  1. waitto warn to room temperature overnight
  2. washwashed with a 5% potassium hydrogensulfate, saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using a gradient of 100% hexane to (60% hexane/ethyl acetate

Sources & evidence

ORD record
ord-f24f45aefd914f6b915b5d51f5cbe266
Source dataset
uspto-grants-1998_09
Patent number
US05807829

Reaction notes

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