Ethyl Acetate → Tert-butyl 2-(4-(hydroxymethyl)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropyl(methyl)carbamate

HRID 1944153Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:42])[CH:13]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][O:31][Si](C(C)C)(C(C)C)C(C)C)=[CH:26][CH:25]=3)[CH2:14][N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1>[OH:31][CH2:30][C:27]1[CH:26]=[CH:25][C:24]([CH:13]([C:12]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[CH:1]=[N:2][CH:3]=[CH:4]3)=[O:42])[CH2:14][N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-((thisopropylsilyloxy)methyl)phenyl)Propyl(methyl)carbamate (E205) in THF under N2 at 0° C. was added TBAF, and the solution was stirred for 30 min at 0° C. The reaction was warmed to room temperature and stirred another 4.5 h. The compound was poured into EtOAc and washed with NH4Cl(sat), dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-20% MeOH/CH2Cl2 gradient) gave pure tert-butyl 2-(4-(hydroxymethyl)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropyl(methyl)carbamate (E205-1)

Workup

temperatureThe reaction was warmed to room temperature
stirringstirred another 4.5 h
washwashed with NH4Cl(sat)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-8e8ab5849adf4ff080ae8d9289d34203
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394826B2

Reaction notes

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