Acetic Acid → HCID 17606704, compound

HRID 2244349Notes

Reaction equation

HRID 2244349 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].CO[C:15]([CH3:17])=[CH2:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 83002-MethoxypropeneHCID 14798Sodium HydroxideHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17606704HCID 17606704, compoundYield 80%

Procedure

To a solution of 500 mg of 2-amino-5-chlorobenzoic acid methyl ester (2.69 mmol) were added slowly 380 μl of 2-methoxypropene (4.04 mmol), 154 μl of acetic acid (2.69 mmol) and 951 mg of sodium triacetoxyborohydride (4.04 mmol). The reaction mixture was stirred at RT for 3.5 d, then 1N NaOH solution was added and the mixture was extracted with DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The remaining residue was purified by column chromatography (silica gel; heptane 100% to heptane/EtOAc 9:1) to give 488 mg (80%) of a yellow liquid. MS (ISP) 228.1 (M+H)+.

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe remaining residue was purified by column chromatography (silica gel; heptane 100% to heptane/EtOAc 9:1)

Sources & evidence

ORD record
ord-4e0ca743476c47dfacac1c80b45ec88a
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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