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Acetic Acid → 3-(1-Ethyl-propylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 852643
Notes
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Reaction equation

HRID 852643 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([NH2:16])[CH:5]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:32][CH2:33][C:34](=O)[CH2:35][CH3:36].CC(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([NH:16][CH:34]([CH2:35][CH3:36])[CH2:33][CH3:32])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7288Ethyl ketoneHCID 5049666Sodium triacetoxyborohydrideHCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

Product 1

HCID 693591323-(1-Ethyl-propylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (200 mg, 0.87 mmol, 1 equiv) in (CH2Cl)2 (5 ml) were added sodium triacetoxyborohydride (1.536 g, 5.22 mmol, 6 equiv), 3-pentanone (0.546 ml, 5.22 mmol, 6 equiv) and AcOH (0.050 ml, 0.87 mmol, 1 equiv). The resulting mixture was stirred at room temperature for 48 h, diluted with CH2Cl2 (20 ml), washed with saturated aqueous NaHCO3 solution (20 ml), dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOH: 3/2) gave 3-(1-ethyl-propylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B43) (106 mg, 40%) as a colourless oil. [M+H]+=305.0 RT=3.19

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOH: 3/2)

Sources & evidence

ORD record
ord-d848f314df9443619dbd002beca5305a
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253198B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes