Sodium Methoxide → HCID 68760936, compound

HRID 1511915Notes

Reaction equation

HRID 1511915 reaction equation
C[O:2][C:3]([C:5]1[N:6]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19]C)=[O:17])[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]=1[Cl:10])=O.C[O-].[Na+]>CO>[CH3:19][O:18][C:16]([C:15]1[C:14](=[O:21])[N:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:6]2[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]([Cl:10])=[C:5]2[C:3]=1[OH:2])=[O:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67230145HCID 67230145, compound

Product 1

HCID 68760936HCID 68760936, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1-[benzyl-(2-ethoxycarbonyl-acetyl)-amino]-3,4,5-trichloro-1H-pyrrole-2-carboxylic acid methyl ester (278 mg, 0.62 mmol) and NaOMe in MeOH (5 mL, 2.5 mmol) in MeOH (3 mL) was refluxed for 4 h; then cooled, the reaction mixture was poured into ice cold 0.5 M HCl solution to quench, the precipitates were collected by filtration and then purified with silica gel column to give the desired product (85 mg) as slightly yellow solid. ESI (m/z): 401 (M+H)+.

Workup

  1. temperaturewas refluxed for 4 h
  2. temperaturethen cooled
  3. customto quench
  4. filtrationthe precipitates were collected by filtration
  5. custompurified with silica gel column

Sources & evidence

ORD record
ord-a941f3d4776144ab8bfb51cec1d92ec3
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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