Hydrochloric Acid → HCID 59497702, compound

HRID 1747418Notes

Reaction equation

HRID 1747418 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH2:6][O:7][CH3:8].Cl.O.C1C[O:23][CH2:22]C1>>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]([N:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:22]1=[O:23])[CH2:6][O:7][CH3:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 59497326HCID 59497326, compound

Product 1

HCID 59497702HCID 59497702, compoundYield 58%

Procedure

To a solution of 3-(2-Amino-phenylamino)-4-methoxy-butyric acid methyl ester (320 mg, 1.3 mmol) in THF (5.0 mL) is added CDT (440 mg, 2.7 mmol) at room temperature. The mixture is stirred at the same temperature for 16 hours. Then 5 mL of 1.0 M HCl solution is added along with 20 mL of water. The mixture is extracted with EtOAc (3×25 mL) and the organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 205 mg (58%) of 4-Methoxy-3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-butyric acid methyl ester.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×25 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-4b65f319f10049eaaead3b756731e3fa
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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