Triacetoxyperiodinane → HCID 178424467, compound

HRID 536950Notes

Reaction equation

[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([CH2:20][OH:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([CH:20]=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1

Participants

Reactant 2

HCID 159087Triacetoxyperiodinane

HCID 178424468HCID 178424468, compound

Product 1

HCID 178424467HCID 178424467, compoundYield 100.4%

Procedure

The title compound was prepared by the procedure of Example 21, step (a) using 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(4-hydroxymethyl-tetrahydro-pyran-4-yl)-phenyl]-amide (as prepared in Example 25, 40.0 mg, 0.0921 mmol) and Dess-Martin periodinane (80.5 mg, 0.184 mmol). The title compound (40 mg, 100%) was obtained as a white solid and used in the next step without further purification. Mass spectrum (ESI, m/z): Calcd. for C25H28N4O3, 433.2 (M+H). found 433.4.

Workup

customThe title compound was prepared by the procedure of Example 21, step (a)

Sources & evidence

ORD record: ord-b26c1f88aa744fb2ba4ea820b21fa6ea
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859602B2

Reaction notes

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