Methanol → HCID 66882697, compound

HRID 1784059Notes

Reaction equation

HRID 1784059 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([CH:11]2[CH2:13][C:12]2([CH3:17])[C:14]([OH:16])=[O:15])=[O:10])=[N:6][CH:7]=1.[CH3:18]O>S(Cl)(Cl)=O>[CH3:18][O:15][C:14]([C:12]1([CH3:17])[CH2:13][CH:11]1[C:9](=[O:10])[NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 66882945HCID 66882945, compound

Product 1

HCID 66882697HCID 66882697, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst2×

Conditions

Temperature
0 °C

Procedure

A suspension of (1SR,2RS)-2-(5-chloro-pyridin-2-ylcarbamoyl)-1-methyl-cyclopropane-carboxylic acid (176 mg) in MeOH (5 ml) was cooled to 0° C. and treated with thionyl chloride (15 drops). After stirring for 2 hrs at 0° C. additional thionyl chloride (10 drops) was added. The clear solution was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2−>CH2Cl2/MeOH 9:1) to give (1SR,2RS)-2-(5-chloro-pyridin-2-ylcarbamoyl)-1-methyl-cyclopropanecarboxylic acid methyl ester (163 mg) as colorless amorphous solid. MS 269.5 ([M+H]+).

Workup

  1. additionwas added
  2. concentrationThe clear solution was concentrated
  3. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2−>CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-23b3204104d74d3296d53d262f0c8187
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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