HCID 68938318, compound → HCID 68943450, compound

HRID 242723Notes

Reaction equation

HRID 242723 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](/[CH:21]=[CH:22]/[C:23]2[C:28]([CH3:30])([CH3:29])[CH2:27][CH2:26][CH2:25][C:24]=2[CH3:31])[CH:16]=1)[C:3]([CH3:14])([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH3:13][C:3]([CH3:14])([C:2](=[O:1])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](/[CH:21]=[CH:22]/[C:23]2[C:28]([CH3:30])([CH3:29])[CH2:27][CH2:26][CH2:25][C:24]=2[CH3:31])[CH:16]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11]

Participants

3

Reactant 2

HCID 68938318HCID 68938318, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 68943450HCID 68943450, compound

Procedure

(E)-Tert-butyl 3-hydroxy-2,2-dimethyl-3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)propylcarbamate (0.0809 g, 0.19 mmol) was reacted with pyridinium chlorochromate according to the method used in Example 56 except that the reaction time was 2 h, 15 min. Purification by flash chromatography (10 to 40% EtOAc-hexanes gradient) gave (E)-tert-butyl 2,2-dimethyl-3-oxo-3-(3-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)phenyl)propylcarbamate as an oil. 1H NMR (400 MHz, CD3OD) δ 7.72 (s, 1H), 7.58 (d, J=7.6 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.35 (t, J=7.6 Hz, 1H), 6.72 (dd, J=16.0, 0.8 Hz, 1H), 6.33 (d, J=16.0 Hz, 1H), 5.05 (t, J=6.0 Hz, 1H), 3.38 (d, J=6.8 Hz, 2H), 2.04 (t, J=6.4 Hz, 2H), 1.76 (s, 3H), 1.61-1.67 (m, 2H), 1.48-1.50 (m, 2H), 1.36-1.42 (m, 15H), 1.06 (s, 6H).

Workup

  1. customPurification by flash chromatography (10 to 40% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-721b2dc1b0934bc6865634a11f6c4064
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

Loading…