Glyoxylic Acid → 4-{[(4-tert-Butyl-phenyl)-carboxy-methyl]-amino}-benzoic Acid Tert-butyl Ester

HRID 1755157Notes

Reaction equation

HRID 1755157 reaction equation
C(OB([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)O)(C)(C)C.[C:14]([OH:18])(=[O:17])[CH:15]=O.[C:19]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([O:23][C:24](=[O:32])[C:25]1[CH:26]=[CH:27][C:28]([NH:31][CH:15]([C:8]2[CH:9]=[CH:10][C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:13]=2)[C:14]([OH:18])=[O:17])=[CH:29][CH:30]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 66584345Tert-butylphenylboronic acid

Product 1

HCID 674862324-{[(4-tert-Butyl-phenyl)-carboxy-methyl]-amino}-benzoic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round bottom flask, t-butyl phenyl boronic acid (850 mg, 4.4 mmol), glyoxylic acid (404 mg, 4.4 mmol) and 4-Amino-benzoic acid tert-butyl ester (780 mg, 4.4 mmol) were dissolved in 25 mL of dichloromethane and allowed to stir at RT. After 30 min the reaction turned cloudy, but was allowed to stir an additional 2 h. Upon completion, the reaction was quenched with 20 mL water and the organic layer was separated, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give 1.6 g (95%). of a light yellow powder. 1H NMR (CDCl3): δ 1.29 (9H, s), 1.55 (9H, s), 5.17 (1H, s), 6.57 (2H, d, J=8.4 Hz), 7.39 (4H, s), 7.78 (2H, d, J=8.4 Hz).

Workup

  1. stirringto stir an additional 2 h
  2. customUpon completion, the reaction was quenched with 20 mL water
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customto give 1.6 g (95%)

Sources & evidence

ORD record
ord-17ad955f984e40dc989d20f65e7f19aa
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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