HCID 67296450, compound → HCID 67313802, compound

HRID 1189935Notes

Reaction equation

HRID 1189935 reaction equation
[CH:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:16]([OH:27])[CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>O=[Mn]=O>[CH:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]([C:16](=[O:27])[CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 67296450HCID 67296450, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67313802HCID 67313802, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

Oxidation of tert-butyl 3-(3-(cyclohexanecarboxamido)phenyl)-3-hydroxypropylcarbamate (37) following the method used in Example 12 except PCC was used in lieu of MnO2 gave tert-butyl 3-(3-(cyclohexanecarboxamido)phenyl)-3-oxopropylcarbamate as a white solid. Yield (0.36 g, 91%); 1H NMR (400 MHz, DMSO-d6) δ 9.97 (s, 1H), 8.15-8.18 (m, 1H), 7.82 (dd, J=1.2, 8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 6.79 (br.t, 1H), 3.24 (q, J=6.0 Hz, 2H), 3.08 (t, J=6.4 Hz, 2H), 2.25-2.35 (m, 1H), 1.69-1.82 (m, 4H), 1.58-1.66 (m, 1H), 1.33 (s, 9H), 1.10-1.44 (m, 5H).

Sources & evidence

ORD record
ord-941de3108e2c4f8a9cb4e8f27bebabf5
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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