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

HRID 2371262Notes

Reaction equation

HRID 2371262 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 EsterYield 189.7%

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

Sources & evidence

ORD record
ord-bd4664df229944e2ab300156d982f669
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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