Acetic Acid → HCID 59497326, compound

HRID 1747417Notes

Reaction equation

HRID 1747417 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5](=O)[CH2:6][O:7][CH3:8].[C:11]1([NH2:18])[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=1.CC(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]([NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH2:18])[CH2:6][O:7][CH3:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 123500Methyl 4-methoxyacetoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 59497326HCID 59497326, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-3-oxo-butyric acid methyl ester (0.67 mL, 5.0 mmol) and Benzene-1,2-diamine (560 mg, 5.5 mmol) are dissolved in DCM (20 mL) and HOAc (0.63 mL, 11 mmol) is added into it. The mixture is stirred for 6 hrs and then NaBH(OAC)3 (3.7 g, 17 mmol) is added and the mixture is stirred for another 60 hr. Then 50 mL of sat. NaHCO3 along with 50 mL of water are added and the mixture is extracted with EtOAc (3×100 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by flash column choromatography affords 320 mg (27%) of 3-(2-Amino-phenylamino)-4-methoxy-butyric acid methyl ester.

Workup

  1. stirringthe mixture is stirred for another 60 hr
  2. extractionthe mixture is extracted with EtOAc (3×100 mL)
  3. customdried
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification by flash column choromatography

Sources & evidence

ORD record
ord-6d41e224b94e4e179622ed9190570c70
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…