Pyridine → HCID 59363831, compound

HRID 1430623Notes

Reaction equation

HRID 1430623 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:23](=[O:25])[CH3:24])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22060556HCID 22060556, compound

Product 1

HCID 59363831HCID 59363831, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-Amino-phenoxy)-2-methyl-propionic acid ethyl ester (0.54 g, 2.42 mmol) in DCM (5 ml) at 0° C. was added pyridine (0.23 ml, 2.9 mmol). The reaction mixture was cooled to 0° C. and a solution of acetyl chloride (0.21 ml, 2.9 mmol) in DCM (4 ml) was added drop wise over 5 min. The reaction mixture was stirred at r.t. for 18 hrs, quenched with water (10 ml) and extracted in DCM (2×20 ml). The organic layer was dried over Na2SO4 and concentrated to afford the crude oil (0.64 g) which was used for the next step without purification.

Workup

  1. customquenched with water (10 ml)
  2. extractionextracted in DCM (2×20 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b321b24836d4ecb90dd7d3fc3c92532
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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