HCID 59966803, compound → HCID 117600819, compound

HRID 1497710Notes

Reaction equation

HRID 1497710 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:19])N(OC)C)([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1>C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:19])[C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 59966803HCID 59966803, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 117600819HCID 117600819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(Methoxy-methyl-carbamoyl)-phenyl]-carbamic acid tert-butyl ester (15.0 g, 1.54 mmol) dissolved in THF (200 mL) is added p-chlorophenylmagnesium bromide (1.0M, 150 mL) at −30° C. The mixture is then stirred at RT overnight. The mixture is quenched with NH4Cl, extracted with ethyl acetate, dried over NaSO4 and concentrated then purified by silica gel. This provides the desired product.

Workup

  1. customThe mixture is quenched with NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated
  5. customthen purified by silica gel

Sources & evidence

ORD record
ord-73e9d768bdb649d88ec0c153d757db61
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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