Triacetoxyperiodinane → HCID 59725889, compound

HRID 1912876Notes

Reaction equation

[C:1]([O:5][C:6](=[O:41])[N:7]([C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][OH:36])=[C:30]([C:37]([F:40])([F:39])[F:38])[CH:29]=2)=[O:26])=[CH:20][CH:19]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6](=[O:41])[N:7]([CH3:8])[C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH:35]=[O:36])=[C:30]([C:37]([F:40])([F:39])[F:38])[CH:29]=2)=[O:26])=[CH:20][CH:19]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

In 50 ml of dichloromethane, 300 mg (0.52 mmol) of [9-(4-{3-[4-(2-hydroxyethyl)-3-(trifluoromethyl)phenyl]-ureido}phenyl)-9H-purin-6-yl]-methyl-carbamic acid tert-butyl ester was dissolved, and 270 mg (0.64 mmol) of Dess-Martin periodinane was added thereto under cooling with ice and the solution was stirred at 0° C. for 20 hours. The reaction solution was partitioned between water and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The product was purified by a silica gel column (ethyl acetate) to obtain 140 mg (47%) of a target product as a colorless amorphous substance.

Workup

temperatureunder cooling with ice
customThe reaction solution was partitioned between water and ethyl acetate
washthe organic layer was washed with a saturated sodium chloride solution
concentrationconcentrated under reduced pressure
customThe product was purified by a silica gel column (ethyl acetate)

Sources & evidence

ORD record: ord-9e9fc649f8cb48f2b30dea4fd0059541
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609656B2

Reaction notes

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