Methanol → HCID 21915164, compound

HRID 2117944Notes

Reaction equation

[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:26][C:27]2[CH:35]=[CH:34][C:30](C(O)=O)=[CH:29][CH:28]=2)=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].C([N:38]([CH2:41]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C[OH:61].[O:62]1CCOC[CH2:63]1>C1(C)C=CC=CC=1>[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:26][C:27]2[CH:35]=[CH:34][C:30]([NH:38][C:41](=[O:61])[O:62][CH3:63])=[CH:29][CH:28]=2)=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 4-{[2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazol-5-yl]methyl}benzoic acid (50 mg) in toluene (0.5 ml) and dioxane (0.5 ml) were added triethylamine (28.1 μl) and diphenylphosphoryl azide (39.1 μl), and the mixture was stirred at 25° C. for 2 hrs., then stirred at 100° C. for 1 h. To the reaction mixture was added methanol (1 ml), and the mixture was refluxed for 2 hrs., and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography over silica gel with chloroform/methanol (20:1) as an eluent to give methyl N-(4-{[2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazol-5-yl]methyl}phenyl)carbamate (17.2 mg).

Workup

stirring, then stirred at 100° C. for 1 h
temperaturethe mixture was refluxed for 2 hrs
concentration, and concentrated in vacuo
customThe residue was purified by preparative thin-layer chromatography over silica gel with chloroform/methanol (20:1) as an eluent

Sources & evidence

ORD record: ord-e93e758bfdf449e880b796d8e8fc0a73
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442715B2

Reaction notes

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