Acetic Acid → HCID 69358777, compound

HRID 852642Notes

Reaction equation

HRID 852642 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+].[CH:32](=O)[CH2:33][CH3:34].CC(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[C:6]([NH:16][CH2:32][CH2:33][CH3:34])[CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

Product 1

HCID 69358777HCID 69358777, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (500 mg, 2,14 mmol, 1 equiv) in (CH2Cl)2 (10 ml) was added sodium triacetoxyborohydride (640 mg, 3.02 mmol, 1.4 equiv), propionaldehyde (0.156 ml, 2.14 mmol, 1 equiv) and CH3COOH (0.125 ml, 2.18 mmol, 1.02 equiv) The resulting mixture was stirred at room temperature for 2 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/AcOEt: 3/2) gave 3-(2-oxo-pyrrolidin-1-yl)-5-propylamino-benzoic acid methyl ester (B35) (250 mg, 42%) as a colourless oil.

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/AcOEt: 3/2)

Sources & evidence

ORD record
ord-aa82c2e2eccf4d09978b02fa50df948a
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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