Methanol → HCID 59340053, compound

HRID 905919Notes

Reaction equation

HRID 905919 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[C:14]([NH:16][CH2:17][C:18]([O:20]C)=[O:19])=[O:15].CO.[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:24][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54681672HCID 54681672, compound

Product 1

HCID 59340053HCID 59340053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.94 g, 1.4 mmol), methanol (0.33 ml, 8.1 mmol) and triphenyl phosphine (0.94 ml, 4.1 mmol) were placed in a 50 mL round bottomed flask with 25 mL of THF. The flask was placed in an ice bath. Diethyl azodicarboxylate (0.64 ml, 4.1 mmol) was added dropwise. A white solid was filtered and this solid was purified by silica flash chromatography (0-3% MeOH/DCM) to give the desired product.

Workup

  1. customThe flask was placed in an ice bath
  2. filtrationA white solid was filtered
  3. customthis solid was purified by silica flash chromatography (0-3% MeOH/DCM)

Sources & evidence

ORD record
ord-5f7691ac0126462daaa3191f37b31fc6
Source dataset
uspto-grants-2011_09
Patent number
US08012968B2

Reaction notes

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