Isobutylamine → 6-hydroxy-N-isobutyl-2,5,7,8-tetramethylchroman-2-carboxamide

HRID 1898689Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:31]([NH2:35])[CH:32]([CH3:34])[CH3:33]>>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH:35][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:16])[CH2:6][CH2:5]2

Participants

Reactant 3

HCID 6558Isobutylamine

HCID 40634Trolox

HCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 672630596-hydroxy-N-isobutyl-2,5,7,8-tetramethylchroman-2-carboxamideYield 75%

Procedure

Following the amide coupling procedure described in protocol A, 510 mg 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (2.04 mmol), 357 mg CDI (2.20 mmol) and 161 mg isobutylamine (2.2 mmol) produced 467 mg of 6-hydroxy-N-isobutyl-2,5,7,8-tetramethylchroman-2-carboxamide as an off-white solid.

Sources & evidence

ORD record: ord-afb97ff7c7dc48f69e73c85b76ab3560
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519001B2

Reaction notes

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