Triacetoxyperiodinane → HCID 178439226, compound

HRID 2090101Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:31]([CH3:33])[CH3:32])[C:6]2[O:10][C:9]([C:11]3[CH:29]=[CH:28][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][C@H:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:30]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:31]([CH3:33])[CH3:32])[C:6]2[O:10][C:9]([C:11]3[CH:29]=[CH:28][C:14]([C:15]([NH:17][CH2:18][C@H:19]4[CH2:20][CH2:21][C@H:22]([CH2:25][CH:26]=[O:27])[CH2:23][CH2:24]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:30]=1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[trans-4-(2-hydroxyethyl)cyclohexyl]methyl}benzamide (50 mg, 0.112 mmol) in dichloromethane (2 ml) was added Dess-Martin periodinane (60 mg, 0.141 mmol). The mixture was stirred for 2 h at 25° C., at which point LC/MS analysis showed no starting material. The mixture was purified by flash chromatography on a Biotage Horizon, 25M column, eluting with 1 column volume of 100% dichloromethane followed by a gradient of 0 to 100% ethyl acetate in dichloromethane over 10 column volumes to provide the title compound (48 mg, 0.108 mmol, 96% yield). Mass spectrum (ESI) 444.0 (M+1).

Workup

customThe mixture was purified by flash chromatography on a Biotage Horizon, 25M column
washeluting with 1 column volume of 100% dichloromethane

Sources & evidence

ORD record: ord-81d77c7c542b40428ff67697342ac63d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436028B2

Reaction notes

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