Trolox → HCID 67263087, compound

HRID 1755587Notes

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=[N:29][CH:28]=[CH:27]2)=O)C=1.[O:31]1C[CH2:34][CH2:33][CH:32]1N>>[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:29][CH2:28][CH:27]1[CH2:34][CH2:33][CH2:32][O:31]1)=[O:16])[CH2:6][CH2:5]2

Participants

Reactant 3

HCID 40634Trolox

HCID 682631,1'-Carbonyldiimidazole

HCID 11412342Tetrahydro-2-furanamine

Product 1

HCID 67263087HCID 67263087, compoundYield 61.8%

Procedure

Following the amide coupling procedure described in protocol A, 496 mg 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1.98 mmol), 376 mg CDI (2.32 mmol) and 404 mg tetrahydrofuranylamine (4.0 mmol) produced 408.0 mg of crude 6-hydroxy-2,5,7,8-tetramethyl-N-((tetrahydrofuran-2-yl)methyl)chroman-2-carboxamide, which was oxidized following protocol B, with 335 mg CAN (0.612 mmol) to yield 74.7 mg of 2-hydroxy-2-methyl-N-((tetrahydrofuran-2-yl)methyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow oil.

Sources & evidence

ORD record: ord-65d238c040984e09b1acc8aea40dd78f
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169196B2

Reaction notes

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