4-Nitrobenzoic Acid → HCID 12074089, compound

HRID 353466Notes

Reaction equation

HRID 353466 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([O:17][C:18](=[O:22])[C@H:19]([CH3:21])[NH2:20])([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:20][C@@H:19]([CH3:21])[C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:22])=[O:10])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 89016L-Alanine 1,1-dimethylethyl ester

Product 1

HCID 12074089HCID 12074089, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of para-nitrobenzoic acid in tetrahydrofuran, 1.2 equivalents of 1,1′-carbonyldiumidazole are added and the mixture is stirred for 30 minutes. Then, 1.1 equivalents of the (S)-L-alanine tert-butyl ester are added and the mixture is stirred for 24 hours at room temperature. The solvent is removed under reduced pressure and the crude is diluted in chloroform and brine. The organic layer is washed with water and dried over MgSO4. The filtrate is concentrated under vacuum and the residue is purified by column chromatography to give the desired compound.

Workup

  1. stirringthe mixture is stirred for 24 hours at room temperature
  2. customThe solvent is removed under reduced pressure
  3. additionthe crude is diluted in chloroform
  4. washThe organic layer is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationThe filtrate is concentrated under vacuum
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-3f6a72d2d06a40daa54b0c3693b480d2
Source dataset
uspto-grants-2004_06
Patent number
US06753340B2

Reaction notes

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