HCID 68825250, compound → HCID 136375597, compound

HRID 1272443Notes

Reaction equation

[CH3:1][C:2]([CH3:50])([CH3:49])[C:3]([O:5][CH:6]([NH2:48])[O:7][C:8](=[O:47])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[C:13]([S:25](=[O:46])(=[O:45])[NH:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][C:30]=2[O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:12]=1)=[O:4]>O1CCCC1.[Pd]>[CH3:50][C:2]([CH3:1])([CH3:49])[C:3]([O:5][CH:6]([NH2:48])[O:7][C:8](=[O:47])[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([S:25](=[O:45])(=[O:46])[NH:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][C:30]=2[O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:12]=1)=[O:4]

Participants

Conditions

Temperature: 30 °C

Procedure

To a stirred solution of 99 mg of amino-[4-benzyloxy-3-[[2-[4-isopropyl-2-(ethoxycarbonylmethoxy)phenyl]ethyl]-sulfamoyl]phenyl]methylenecarbamoyloxymethyl 2,2-dimethylpropionate in 3 mL of tetrahydrofuran was added 9.2 mg of 10% palladium on carbon under ice-cooling, and the mixture was stirred under a hydrogen atmosphere at 30° C. for 1 hour. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 75 mg of amino-[4-hydroxy-3-[[2-[4-isopropyl-2-(ethoxycarbonylmethoxy)phenyl]ethyl]sulfamoyl]-phenyl]methylenecarbamoyloxymethyl 2,2-dimethylpropionate.

Workup

temperaturecooling
customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record: ord-071c546395b645a5b546b2e71721d152
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208524B2

Reaction notes

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