HCID 67296648, compound → HCID 68524158, compound

HRID 1189948Notes

Reaction equation

HRID 1189948 reaction equation
[CH2:1]([CH:3]([CH2:24][CH3:25])[CH2:4][NH:5][C:6]1[CH:7]=[C:8]([CH:12]([OH:23])[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[CH:10][CH:11]=1)[CH3:2]>O=[Mn]=O>[CH2:24]([CH:3]([CH2:1][CH3:2])[CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:12](=[O:23])[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH:9]=[CH:10][CH:11]=1)[CH3:25]

Participants

3

Reactant 1

HCID 67296648HCID 67296648, compound

Product 1

HCID 68524158HCID 68524158, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

Oxidation of tert-butyl 3-(3-(2-ethylbutylamino)phenyl)-3-hydroxypropylcarbamate by MnO2 following the method used in Example 12 gave tert-butyl 3-(3-(2-ethylbutylamino)phenyl)-3-oxopropylcarbamate as a pale yellow oil. Yield (0.350 g, 86%); 1H NMR (400 MHz, DMSO-d6+5% D2O) δ 7.17 (t, J=7.6 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.04 (s, 1H), 6.79 (d, J=7.6 Hz, 1H), 3.20 (t, J=6.4 Hz, 2H), 3.03 (t, J=6.8 Hz, 2H), 2.90 (d, J=6.0 Hz, 2H), 1.50-1.44 (m, 1H), 1.31 (s, 9H), 1.28-1.19 (m, 4H), 0.82 (t, J=7.6 Hz, 6H).

Sources & evidence

ORD record
ord-59338d8dd7914a18bb0c56b7067bce67
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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