Glyoxylic Acid → 2-[4-(tert-Butoxycarbonylamino)phenyl]-2-[isopropyl(methyl)amino]acetic Acid

HRID 888441Notes

Reaction equation

HRID 888441 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>C1(C)C=CC=CC=1>[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:2]([N:13]([CH:14]([CH3:19])[CH3:15])[CH3:11])[C:1]([OH:5])=[O:4])=[CH:16][CH:15]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 3613184(4-Boc-Aminophenyl)Boronic Acid

Product 1

HCID 576251192-[4-(tert-Butoxycarbonylamino)phenyl]-2-[isopropyl(methyl)amino]acetic AcidYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with glyoxylic acid (618 mg, 6.72 mmol), toluene (20 mL), N,N-isopropylmethylamine (486 mg, 6.60 mmol) and 4-(tert-butoxycarbonylamino) phenylboronic acid (1.58 g, 6.66 mmol). The reaction was sealed with a plastic cap under a nitrogen atmosphere and stirred at room temperature for 7 d. After this time, the reaction was concentrated under reduced pressure. The resulting residue was subjected to flash chromatography to afford 25 in 62% yield (1.34 g) as a light brown solid: mp 320° C. dec, 1H NMR (300 MHz, DMSO-d6) δ 9.42 (s, 1H), 7.42 (d, 2H, J=8.7 Hz), 7.37 (d, 2H, J=8.7 Hz), 4.23 (s, 1H), 3.28 (m, 1H), 3.17 (s, 1H), 2.23 (s, 3H), 1.47 (s, 9H), 1.15 (d, 3H, f=6.6 Hz), 1.11 (d, 3H, J=6.6 Hz); MS (ESI+) m/z 323 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customThe reaction was sealed with
  3. customa plastic cap under a nitrogen atmosphere
  4. concentrationAfter this time, the reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a29a982e27f04f5c84c0c9ed8c2d1e04
Source dataset
uspto-grants-2012_08
Patent number
US08247550B2

Reaction notes

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