HCID 22418293, compound → HCID 22418301, compound

HRID 1720381Notes

Reaction equation

HRID 1720381 reaction equation
C([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([NH:11][C:12](=[O:28])[CH:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH2:14][S:15]C(=O)C)[CH:10]=1)=[O:5])C>C(OCC)(=O)C>[C:4]([C:6]1[NH:7][CH:8]=[C:9]([NH:11][C:12](=[O:28])[CH:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH2:14][SH:15])[CH:10]=1)([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 22418293HCID 22418293, compound

Product 1

HCID 22418301HCID 22418301, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By working in a way similar to that described in example 17 and by using N-(2-ethoxycarbonyl-4-pyrrolyl)-3-acetylthio-2-(3-methoxybenzyl)-propanamide (0.98 g; 2.42 mmoles), prepared as described in example 24, a crude was obtained which, chromatographed on silica gel (eluent CH2Cl2 :CH3OH:CH3COOH=90:10:1) and collected with ligroin:ethyl acetate=1:1 afforded N-(2-carboxy-4-pyrrolyl)-3-mercapto-2-(3-methoxybenzyl)-propanamide (0.520 g; 64.2% yield) as white solid.

Workup

  1. customprepared
  2. customa crude was obtained which
  3. customchromatographed on silica gel (eluent CH2Cl2 :CH3OH:CH3COOH=90:10:1)
  4. customcollected with ligroin

Sources & evidence

ORD record
ord-4a3e5c50586c4948a736e172e273db1c
Source dataset
uspto-grants-1996_04
Patent number
US05506259

Reaction notes

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